Information on EC 2.4.2.28 - S-methyl-5'-thioadenosine phosphorylase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea

EC NUMBER
COMMENTARY hide
2.4.2.28
-
RECOMMENDED NAME
GeneOntology No.
S-methyl-5'-thioadenosine phosphorylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pentosyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Cysteine and methionine metabolism
-
-
Metabolic pathways
-
-
polyamine pathway
-
-
S-methyl-5'-thioadenosine degradation II
-
-
SYSTEMATIC NAME
IUBMB Comments
S-methyl-5'-thioadenosine:phosphate S-methyl-5-thio-alpha-D-ribosyl-transferase
Also acts on 5'-deoxyadenosine and other analogues having 5'-deoxy groups.
CAS REGISTRY NUMBER
COMMENTARY hide
61970-06-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
Caldariella acidophila
-
-
-
Manually annotated by BRENDA team
Escherichia coli O157:H7 EDL933
O157:H7 EDL933
-
-
Manually annotated by BRENDA team
Wistar
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strains BB170 and BB120
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2',3'-dideoxyadenosine + phosphate
adenine + 2,3-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
substrate for trypanosomal but not for mammalian enzyme
-
-
?
2'-deoxy-2'-amino-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-2-amino-5-thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxy-2'-azido-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-2-azido-5-thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxy-2-fluoro-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-2-fluoro-5-thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxy-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-5-thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxyadenosine + phosphate
adenine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
2-amino-5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
2-aminoadenosine + 5-hydroxyethylthio-D-ribose 1-phosphate
show the reaction diagram
-
28% activity compared to 5'-methyladenosine or 5'-deoxy-5'-(hydroxyethylthio)adenosine
-
-
?
2-chloro-2'-deoxyadenosine + phosphate
2-chloroadenine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
r
2-chloro-5'-O-methyl-2'-deoxyadenosine + phosphate
2-chloroadenine + 5-O-methyl-2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
r
2-chloroadenosine + phosphate
2-chloroadenine + D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
r
2-fluoro-5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
2-fluoroadenosine + 5-hydroxyethylthio-D-ribose 1-phosphate
show the reaction diagram
-
149% activity compared to 5'-methyladenosine or 5'-deoxy-5'-(hydroxyethylthio)adenosine
-
-
?
3'-deoxy-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 3-deoxy-5-thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
3'-deoxyadenosine + phosphate
adenine + 3-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
substrate for trypanosomal but not for mammalian enzyme
-
-
?
5'-butylthioadenosine + phosphate
adenine + 5-butylthio-D-ribose 1-phosphate
show the reaction diagram
5'-chloroadenosine + phosphate
adenine + 5-deoxy-5-chloro-D-ribose 1-phosphate
show the reaction diagram
5'-deoxy-5'-(1,3-thiazol)-2-yl-sulfanyladenosine + phosphate
adenine + 5-(1,3-thiazol-2-yl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(2-(pyridin-2-yl)ethyl)-thioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(2-methylbutyl)-thioadenosine + phosphate
adenine + 5-(2-methylbutyl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(2-methylphenyl)-thioadenosine + phosphate
adenine + 5-(2-methylphenyl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(3-methylphenyl)-thioadenosine + phosphate
adenine + 5-(3-methylphenyl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(4-methoxyphenyl)-thioadenosine + phosphate
adenine + 5-(4-methoxyphenyl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(4-methylphenyl)-thioadenosine + phosphate
adenine + 5-(4-methylphenyl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
adenine + 5-hydroxyethylthio-D-ribose 1-phosphate
show the reaction diagram
5'-deoxy-5'-(phenylethyl)-thioadenosine + phosphate
adenine + 5-phenylethylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(phenylmethyl)-thioadenosine + phosphate
adenine + 5-phenylmethylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-(quinolin-2-yl)-sulfanyladenosine + phosphate
adenine + 5-(quinolin-2-yl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-butylthioadenosine + phosphate
adenine + 5-butylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-cyclohexyl-thioadenosine + phosphate
adenine + 5-cyclohexylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-cyclopentyl-thioadenosine + phosphate
adenine + 5-cyclopentylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-hydroxyethylthioadenosine + phosphate
adenine + 5-(2-hydroxyethyl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-imidazol-2-yl-sulfanyladenosine + phosphate
adenine + 5-(imidazol-2-yl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-isobutylthioadenosine + phosphate
adenine + 5-isobutylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-isopentylthioadenosine + phosphate
adenine + 5-isopentylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-methyl-thioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
5'-deoxy-5'-phenyl-thioadenosine + phosphate
adenine + 5-phenylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-phenylmethylene-adenosine + phosphate
adenine + 5-deoxy-5-phenylmethylene-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-pyridin-2-yl-sulfanyladenosine + phosphate
adenine + 5-(pyridin-2-yl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-pyridin-4-yl-sulfanyladenosine + phosphate
adenine + 5-(pyridin-4-yl)thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-tert-butylthioadenosine + phosphate
adenine + 5-tert-butylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'-[4-(trifluoromethyl)phenyl]-thioadenosine + phosphate
adenine + 5-[4-(trifluoromethyl)phenyl]thio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5'phenylaminoadenosine + phosphate
adenine + 5-deoxy-5-phenylamino-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-adenosine + phosphate
adenine + 5-thio-D-ribose 1 phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxyadenosine + phosphate
adenine + 5-deoxy-D-ribose 1-phosphate
show the reaction diagram
5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
show the reaction diagram
5'-iodo-5'-deoxyadenosine + phosphate
adenine + 5-iodo-5-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
r
5'-iodoadenosine + phosphate
adenine + 5-deoxy-5-iodo-D-ribose 1-phosphate
show the reaction diagram
5'-isobutylthioadenosine + phosphate
adenine + 5-isobutylthio-D-ribose 1-phosphate
show the reaction diagram
5'-isobutylthioinosine + phosphate
hypoxanthine + 5-isobutylthio-D-ribose 1-phosphate
show the reaction diagram
Caldariella acidophila
-
8.1% of the reaction with 5'-methylthioadenosine
-
-
?
5'-methylselenoadenosine + phosphate
adenine + 5-methylseleno-D-ribose 1-phosphate
show the reaction diagram
-
95% of the activity with 5'-methylthioadenosine
-
-
?
5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
5'-methylthioadenosine + phosphate
adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
?
5'-methylthioinosine + phosphate
hypoxanthine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
5'-n-butylthioadenosine + phosphate
adenine + 5-n-butylthio-D-ribose 1-phosphate
show the reaction diagram
Caldariella acidophila
-
93.3% of the reaction with 5'-methylthioadenosine
-
-
?
5'-n-propylthioadenosine + phosphate
adenine + 5-n-propylthio-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-phenyladenosine + phosphate
adenine + 5-phenyl-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-phenylthioadenosine + phosphate
adenine + 5-phenylthio-D-ribose 1-phosphate
show the reaction diagram
6-methylpurine 2'-deoxyribonucleoside + phosphate
6-methylpurine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
substrate for trypanosomal but not for mammalian enzyme
-
-
?
9-[2-deoxy-beta-D-ribofuranosyl]-6-methylpurine + phosphate
?
show the reaction diagram
-
a toxic prodrug, 5% of the activity with S-methyl-5'-thioadenosine
-
-
?
9-[6-deoxy-beta-L-talofuranosyl]-2-F-adenine + phosphate
?
show the reaction diagram
-
a toxic prodrug, 23% of the activity with S-methyl-5'-thioadenosine
-
-
?
adenosine + phosphate
adenine + D-ribose 1-phosphate
show the reaction diagram
guanosine + phosphate
guanine + D-ribose 1-phosphate
show the reaction diagram
inosine + phosphate
hypoxanthine + D-ribose 1-phosphate
show the reaction diagram
S-adenosyl-L-homocysteine + phosphate
?
show the reaction diagram
0.81% activity compared to activity with 5'-methylthioadenosine
-
-
?
S-adenosylhomocysteine + ?
?
show the reaction diagram
-
-
-
-
?
S-adenosylhomocysteine + phosphate
?
show the reaction diagram
14% relative activity
-
-
?
S-methyl-5'-thioadenosine + arsenate
adenine + S-methyl-5-thio-alpha-D-ribose 1-arsenate
show the reaction diagram
-
arsenolysis
-
-
?
S-methyl-5'-thioadenosine + phosphate
adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
adenine + 5-hydroxyethylthio-D-ribose 1-phosphate
show the reaction diagram
5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
adenosine + phosphate
adenine + D-ribose 1-phosphate
show the reaction diagram
guanosine + phosphate
guanine + D-ribose 1-phosphate
show the reaction diagram
P50389
-
-
-
-
inosine + phosphate
hypoxanthine + D-ribose 1-phosphate
show the reaction diagram
P50389
-
-
-
-
S-methyl-5'-thioadenosine + phosphate
adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no requirement for metal ion, e.g. Mg2+, Mn2+ or Ca2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-cis-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
-
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(1H-1,2,3-triazol-4-yl)pyrrolidine
-
-
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(penta-3-yl)pyrrolidine
-
-
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-isobutylpyrrolidine
-
-
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
-
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethynyl-3-hydroxypyrrolidine
-
-
(+/-)-trans-4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(+/-)-trans-4-(cyclohexylmethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(+/-)-trans-4-allyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(+/-)-trans-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(+/-)-trans-4-cyclopropyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(+/-)-trans-4-[3-(benzylthio)propyl]-1-[(9-deazaadenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-di-deoxy-1,4-imino-5-methylthio-D-ribitol
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(1-naphthyl)thio-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(3-methylphenyl)thio-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(4-methylphenyl)thio-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-O-methyl-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-phenylthio-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-(2-fluoroethyl)thio-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-(2-hydroxyethyl)thio-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-(4-fluorophenyl)thio-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-ethylthio-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-n-propylthio-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-imino-1,4,5,6,7-penta-deoxy-D-ribo-heptitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-imino-1,4,5-trideoxy-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-5-(3-chlorophenyl)thio-1,4-dideoxy-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-5-(4-chlorophenyl)thio-1,4-dideoxy-1,4-imino-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-5-benzylthio-1,4-dideoxy-1,4-imino-D-ribitol
-
-
(3R,4R)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-methoxymethylpyrrolidine
-
-
(3R,4R)-4-(benzyloxymethyl)-1-[(9-deaza-adenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-1-[(8-aza-9-deazaadenin-9-yl)methyl]-4-benzylthiomethyl-3-hydroxypyrrolidine hydrochloride
-
-
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-(1-propylthiomethyl)pyrrolidine
-
-
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-(2-propylthiomethyl)pyrrolidine
-
-
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-(4-pyridylthiomethyl)pyrrolidine
-
-
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-phenylthiomethylpyrrolidine
-
-
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-4-(4-fluorophenylthiomethyl)-3-hydroxypyrrolidine
-
-
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-4-ethylthiomethyl-3-hydroxypyrrolidine
-
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(1-propyl)pyrrolidine
-
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(4-chlorophe-nylthiomethyl)pyrrolidine
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)pyrrolidine
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-methylthiomethylpyrrolidine
-
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
-
(3R,4S)-1-[(9-deazaadenin-9yl)methyl]-3-hydroxy-4-(methylthio-methyl) pyrrolidine
-
treatment of cultured FaDu and Cal27 cells with 0.001 mM (3R,4S)-1-[(9-deazaadenin-9yl)methyl]-3-hydroxy-4-(methylthio-methyl) pyrrolidine and 0.02 mM 5'-methylthioadenosine inhibits MTAP by 96%, increases cellular 5'-methylthioadenosine concentrations, decreases polyamines, and induces apoptosis
(3R,4S)-4-(1-butylthiomethyl)-1-[(9-deaza-adenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-4-(3-chlorophenylthiomethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-4-(4-chlorophenylthiomethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-4-benzylthiomethyl-1-[(9-deazaadenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-4-cyclohexylthiomethyl-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
2'-deoxyguanosine
-
-
2'-deoxyinosine
-
weak, competitive
2-bromo-9-(1,3-dihydroxy-2-propoxymethyl)adenine
-
strong
2-bromo-9-(2-hydroxyethoxymethyl)adenine
-
-
2-chloro-9-(1,3-dihydroxy-2-propoxymethyl)adenine
-
strong
2-chloro-9-(2-hydroxyethoxymethyl)adenine
-
-
2-Deoxyribose 1-phosphate
-
-
2-iodo-9-(1,3-dihydroxy-2-propoxymethyl)adenine
-
strong
2-iodo-9-(2-hydroxyethoxymethyl)adenine
-
-
5'-butylthio-DADMe-ImmucillinA
5'-Chloroformycin
-
-
5'-Deoxy-5'-chloroformycin
-
competitive
5'-deoxy-5'-methylthiotubercidin
-
-
5'-deoxy-adenosine
-
and analogues; strong, competitive
5'-dimethylthioadenosine
5'-ethylthio-DADMe-ImmucillinA
-
inhibits quorum sensing induction completely at 0.001 mM
5'-ethylthioadenosine
-
-
5'-methylthio-DADMe-immucillin A
-
5'-methylthio-DADMe-ImmucillinA
5'-methylthio-immucillin-adenine
-
i.e. MT-immucillin-A
-
5'-methylthiotubercidin
5'-n-Propylthioadenosine
-
-
9-(phosphonoalkyl)adenine
-
-
-
9-(phosphonoheptyl)adenine
-
-
-
9-[(1-Hydroxy-3-iodo-2-propoxy)methyl]adenine
adenine
adenine arabinoside
-
weak, competitive
adenosine
-
strong, competitive
calcineurin B-like 3
-
inhibits only in the presence of Ca2+, MTAN interacts specifically with calcineurin B-like 3, but not with calcineurin B-like 1 and calcineurin B-like 4. The 91-amino acid region of calcineurin B-like 3 is sufficient for the interaction with MTAN. Calcineurin B-like 3 and MTAN associate with each other in plant cells, they interact in vitro and in vivo, form a complex outside of the nucleus, colocalize mainly at the plasma membrane
-
dithiothreitol
-
0.8 M, reduction of thermostability
DTNB
-
-
Formycin A
fructose 1-phosphate
-
-
guanidine hydrochloride
-
only recombinant enzyme
Guanine
guanosine
-
weak, competitive
hydrogen peroxide
Inosine
-
weak, competitive
iodoacetamide
iodoacetate
L-methionine
-
weak
MT-ImmA
-
i.e. (3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-methylthiomethylpyrrolidine
N-ethylmaleimide
-
5'-methylthioadenosine partly protects
p-chloromercuribenzoic acid
p-Cl-PhT-DADMe-ImmA
-
-
proteinase K
-
recombinant enzyme, 10% remaining activity after 4 h at 37C, phosphate protects
-
ribose 1-phosphate
-
-
S-adenosyl-L-homocysteine
SH-group blocking compounds
Subtilisin
-
recombinant enzyme, 24% remaining activity after 4 h at 37C, phosphate protects
-
tert-butyl hydroperoxide
tert-butyl trans-3-hydroxy-4-vinylpyrrolidine-1-carboxylate
-
-
trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine
-
-
trans-4-cyclopentyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dithiothreitol
putrescine
SH-group reducing agents
spermidine
-
increases activity
spermine
-
increases activity
additional information
-
imidazole buffer is the best buffer, whereas phosphate and HEPES buffers result in enzyme velocities that are only 50-60% of those for imidazole; imidazole buffer is the best buffer, whereas phosphate and HEPES buffers result in enzyme velocities that are only 50-60% of those for imidazole
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.6
2'-deoxy-2'-azido-5'-deoxy-5'-methylthioadenosine
-
-
0.0031
2'-deoxy-5'-deoxy-5'-methylthioadenosine
-
-
0.0039
3'-deoxy-5'-deoxy-5'-methylthioadenosine
-
-
0.009
5'-deoxy-5'-(1,3-thiazol)-2-yl-sulfanyladenosine
-
-
0.005
5'-deoxy-5'-(2-(pyridin-2-yl)ethyl)-thioadenosine
-
-
0.0028
5'-deoxy-5'-(2-methylbutyl)-thioadenosine
-
-
0.002
5'-deoxy-5'-(2-methylphenyl)-thioadenosine
-
-
0.0015
5'-deoxy-5'-(3-methylphenyl)-thioadenosine
-
-
0.0032
5'-deoxy-5'-(4-methoxyphenyl)-thioadenosine
-
-
0.0017
5'-deoxy-5'-(4-methylphenyl)-thioadenosine
-
-
0.0046
5'-deoxy-5'-(phenylethyl)-thioadenosine
-
-
0.0034
5'-deoxy-5'-(phenylmethyl)-thioadenosine
-
-
0.0052
5'-deoxy-5'-(quinolin-2-yl)-sulfanyladenosine
-
-
0.0031
5'-deoxy-5'-butylthioadenosine
-
-
0.00102
5'-deoxy-5'-cyclohexyl-thioadenosine
-
-
0.0035
5'-deoxy-5'-cyclopentyl-thioadenosine
-
-
0.03
5'-deoxy-5'-ethylthioadenosine
-
-
0.004
5'-deoxy-5'-hydroxyethylthioadenosine
-
-
0.003
5'-deoxy-5'-imidazol-2-yl-sulfanyladenosine
-
-
0.0018
5'-deoxy-5'-isobutylthioadenosine
-
-
0.017
5'-deoxy-5'-isopentylthioadenosine
-
-
0.0018
5'-deoxy-5'-methyl-thioadenosine
-
-
0.00001 - 0.026
5'-deoxy-5'-methylthioadenosine
0.0069
5'-deoxy-5'-phenyl-thioadenosine
-
-
0.00088
5'-deoxy-5'-pyridin-2-yl-sulfanyladenosine
-
-
0.005
5'-deoxy-5'-pyridin-4-yl-sulfanyladenosine
-
-
0.025
5'-deoxy-5'-tert-butylthioadenosine
-
-
0.007
5'-deoxy-5'-[4-(trifluoromethyl)phenyl]-thioadenosine
-
-
0.006
5'-deoxy-adenosine
-
-
0.0043 - 0.023
5'-deoxyadenosine
0.00047 - 0.3
5'-methylthioadenosine
0.008
5-methylthioribose 1-phosphate
-
-
0.023
adenine
-
-
0.0254 - 0.184
adenosine
0.1136 - 0.916
guanosine
0.084 - 0.963
Inosine
0.123 - 13.5
phosphate
0.2009
S-adenosylhomocysteine
-
-
0.005
S-methyl-5'-thioadenosine
-
pH 7.5, 25C
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04
2'-deoxy-2'-azido-5'-deoxy-5'-methylthioadenosine
Homo sapiens
-
-
0.0004
2'-deoxy-2-fluoro-5'-deoxy-5'-methylthioadenosine
Homo sapiens
-
-
0.28
2'-deoxy-5'-deoxy-5'-methylthioadenosine
Homo sapiens
-
-
0.004
3'-deoxy-5'-deoxy-5'-methylthioadenosine
Homo sapiens
-
-
3.8
5'-deoxy-5'-(1,3-thiazol)-2-yl-sulfanyladenosine
Homo sapiens
-
-
2.14
5'-deoxy-5'-(2-(pyridin-2-yl)ethyl)-thioadenosine
Homo sapiens
-
-
5.5
5'-deoxy-5'-(2-methylbutyl)-thioadenosine
Homo sapiens
-
-
2.4
5'-deoxy-5'-(2-methylphenyl)-thioadenosine
Homo sapiens
-
-
1.4
5'-deoxy-5'-(3-methylphenyl)-thioadenosine
Homo sapiens
-
-
1.5
5'-deoxy-5'-(4-methoxyphenyl)-thioadenosine
Homo sapiens
-
-
0.3
5'-deoxy-5'-(4-methylphenyl)-thioadenosine
Homo sapiens
-
-
2.5
5'-deoxy-5'-(phenylethyl)-thioadenosine
Homo sapiens
-
-
2.49
5'-deoxy-5'-(phenylmethyl)-thioadenosine
Homo sapiens
-
-
3.44
5'-deoxy-5'-(quinolin-2-yl)-sulfanyladenosine
Homo sapiens
-
-
2.3
5'-deoxy-5'-butylthioadenosine
Homo sapiens
-
-
1.01
5'-deoxy-5'-cyclohexyl-thioadenosine
Homo sapiens
-
-
1.57
5'-deoxy-5'-cyclopentyl-thioadenosine
Homo sapiens
-
-
0.67
5'-deoxy-5'-ethylthioadenosine
Homo sapiens
-
-
5.9
5'-deoxy-5'-hydroxyethylthioadenosine
Homo sapiens
-
-
1.5
5'-deoxy-5'-imidazol-2-yl-sulfanyladenosine
Homo sapiens
-
-
2.9
5'-deoxy-5'-isobutylthioadenosine
Homo sapiens
-
-
0.85
5'-deoxy-5'-isopentylthioadenosine
Homo sapiens
-
-
4.6
5'-deoxy-5'-methyl-thioadenosine
Homo sapiens
-
-
3.16
5'-deoxy-5'-phenyl-thioadenosine
Homo sapiens
-
-
0.23
5'-deoxy-5'-pyridin-2-yl-sulfanyladenosine
Homo sapiens
-
-
4.2
5'-deoxy-5'-pyridin-4-yl-sulfanyladenosine
Homo sapiens
-
-
1.46
5'-deoxy-5'-tert-butylthioadenosine
Homo sapiens
-
-
0.8
5'-deoxy-5'-[4-(trifluoromethyl)phenyl]-thioadenosine
Homo sapiens
-
-
4.8
5'-deoxy-adenosine
Homo sapiens
-
-
0.4 - 24.5
5'-methylthioadenosine
22.8 - 43.6
adenosine
7.31 - 29.6
guanosine
9.38 - 132
Inosine
0.26
phosphate
Mycobacterium tuberculosis
O06401
pH and temperature not specified in the publication, co-substrate: 0.2 mM 5'-methylthioadenosine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
588 - 2600
5'-methylthioadenosine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000018
(+/-)-cis-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000002
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(1H-1,2,3-triazol-4-yl)pyrrolidine
-
pH 7.4, 25C
0.0000007
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(penta-3-yl)pyrrolidine
-
pH 7.4, 25C
0.000000047
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-isobutylpyrrolidine
-
pH 7.4, 25C
0.00000084
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.00000039
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethynyl-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000000064
(+/-)-trans-4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000000059
(+/-)-trans-4-(cyclohexylmethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.00000035
(+/-)-trans-4-allyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000000009
(+/-)-trans-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000000063
(+/-)-trans-4-cyclopropyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000000054
(+/-)-trans-4-[3-(benzylthio)propyl]-1-[(9-deazaadenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.000026
(1S)-1-(9-deazaadenin-9-yl)-1,4-di-deoxy-1,4-imino-5-methylthio-D-ribitol
pH 7.0, 25C
0.00009
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(1-naphthyl)thio-D-ribitol
-
pH 7.4, 25C
0.00000139
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(3-methylphenyl)thio-D-ribitol
-
pH 7.4, 25C
0.0000044
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(4-methylphenyl)thio-D-ribitol
-
pH 7.4, 25C
0.000026
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol
-
pH 7.4, 25C
0.000134
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-O-methyl-D-ribitol
-
pH 7.4, 25C
0.0000036
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-phenylthio-D-ribitol
-
pH 7.4, 25C
0.00002
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-(2-fluoroethyl)thio-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.000056
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-(2-hydroxyethyl)thio-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.0000064
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-(4-fluorophenyl)thio-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.0000092
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-ethylthio-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.000004
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-5-n-propylthio-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.000044
(1S)-1-(9-deazaadenin-9-yl)-1,4-imino-1,4,5,6,7-penta-deoxy-D-ribo-heptitol
-
pH 7.4, 25C
0.00072
(1S)-1-(9-deazaadenin-9-yl)-1,4-imino-1,4,5-trideoxy-D-ribitol
-
pH 7.4, 25C
0.0000064
(1S)-1-(9-deazaadenin-9-yl)-5-(3-chlorophenyl)thio-1,4-dideoxy-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.000000576
(1S)-1-(9-deazaadenin-9-yl)-5-(4-chlorophenyl)thio-1,4-dideoxy-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.000026
(1S)-1-(9-deazaadenin-9-yl)-5-benzylthio-1,4-dideoxy-1,4-imino-D-ribitol
-
pH 7.4, 25C
0.000085
(3R,4R)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-methoxymethylpyrrolidine
-
pH 7.5, 25C
0.000022
(3R,4R)-4-(benzyloxymethyl)-1-[(9-deaza-adenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.000055
(3R,4S)-1-[(8-aza-9-deazaadenin-9-yl)methyl]-4-benzylthiomethyl-3-hydroxypyrrolidine hydrochloride
-
pH 7.5, 25C
0.0000013
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-(1-propylthiomethyl)pyrrolidine
-
pH 7.5, 25C
0.0000009
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-(2-propylthiomethyl)pyrrolidine
-
pH 7.5, 25C
0.000014
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-(4-pyridylthiomethyl)pyrrolidine
-
pH 7.5, 25C
0.0000015
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-phenylthiomethylpyrrolidine
-
pH 7.5, 25C
0.000002
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-4-(4-fluorophenylthiomethyl)-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.00000065
(3R,4S)-1-[(9-deaza-adenin-9-yl)methyl]-4-ethylthiomethyl-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.002
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(1-propyl)pyrrolidine
-
above, pH 7.5, 25C
0.00000036 - 0.00000175
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)pyrrolidine
0.0000017
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-methylthiomethylpyrrolidine
-
pH 7.5, 25C
0.00000031
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.00000028
(3R,4S)-4-(1-butylthiomethyl)-1-[(9-deaza-adenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.00000081
(3R,4S)-4-(3-chlorophenylthiomethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.000002
(3R,4S)-4-(4-chlorophenylthiomethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.0000014
(3R,4S)-4-benzylthiomethyl-1-[(9-deazaadenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.0000000034
(3R,4S)-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
0.00000076
(3R,4S)-4-cyclohexylthiomethyl-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.5, 25C
0.0002 - 0.0007
2-bromo-9-(1,3-dihydroxy-2-propoxymethyl)adenine
-
-
0.001 - 0.01
2-bromo-9-(2-hydroxyethoxymethyl)adenine
-
-
0.0002 - 0.0007
2-chloro-9-(1,3-dihydroxy-2-propoxymethyl)adenine
-
-
0.001 - 0.01
2-chloro-9-(2-hydroxyethoxymethyl)adenine
-
-
0.0002 - 0.0007
2-iodo-9-(1,3-dihydroxy-2-propoxymethyl)adenine
-
-
0.001 - 0.01
2-iodo-9-(2-hydroxyethoxymethyl)adenine
-
-
0.0083 - 0.031
5'-methylthiotubercidin
0.015
9-(phosphonoheptyl)adenine
-
low phosphate concentration of 3.5 mM
-
0.172
adenine
-
-
0.048
Formycin A
-
at 0.05 mM
0.000026
MT-ImmA
-
pH 7.5, 25C
0.00000003
tert-butyl trans-3-hydroxy-4-vinylpyrrolidine-1-carboxylate
-
pH 7.4, 25C
0.00000065
trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine
-
pH 7.4, 25C
0.000000013
trans-4-cyclopentyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
pH 7.4, 25C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000001 - 0.000125
5'-butylthio-DADMe-ImmucillinA
0.00000011 - 0.00000014
5'-ethylthio-DADMe-ImmucillinA
0.000025 - 0.000075
5'-methylthio-DADMe-immucillin A
0.000000105 - 0.0006
5'-methylthio-DADMe-ImmucillinA
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0234
-
purified enzyme
0.0283
-
partially purified enzyme
0.048
-
substrate 2-amino-5'-deoxy-5'-(hydroxyethylthio)adenosine
0.092
-
partially purified enzyme, forward reaction, substrate 5'-methylthioadenosine
0.131
-
purified enzyme
0.17
-
substrate 5'-methyladenosine or 5'-deoxy-5'-(hydroxyethylthio)adenosine
0.25
-
substrate 2-fluoro-5'-deoxy-5'-(hydroxyethylthio)adenosine
0.26
-
substrate 5'-deoxyadenosine, forward reaction
0.365
-
substrate 5'-deoxy-5'-(hydroxyethylthio)adenosine, preincubation with substrate
0.38
-
with adenosine as substrate
0.46
-
with 5'-choroadenosine as substrate
0.67
-
purified enzyme
0.83
-
with 5'-choroadenosine as substrate
0.96
-
with S-adenosylhomocysteine as substrate
1.06
-
with 5'-iodoadenosine as substrate
1.36
-
with 5'-phenylthioadenosine as substrate
1.5
-
with 5'-butylthioadenosine as substrate
1.85
-
with 5'-isobutylthioadenosine as substrate
1.98
-
with 5'-isobutylthioadenosine as substrate
2.44
-
with 5'-phenylthioadenosine as substrate
2.46
Caldariella acidophila
-
purified enzyme
2.48
Caldariella acidophila
-
purified enzyme
2.6
-
with 5'-ethylthioadenosine as substrate
2.72
-
with 5'-butylthioadenosine as substrate
3.14
-
with 5'-iodoadenosine as substrate
4.42
-
with 5'-ethylthioadenosine as substrate
4.86
-
70C, pH 7.4, mutant enzyme C259S/C261S/C262S/C200S/C205S
4.97
-
70C, pH 7.4, mutant enzyme C262S
5.09
-
70C, pH 7.4, mutant enzyme C259S/C261S
5.28
-
70C, pH 7.4, mutant enzyme C259S/C261S/C262S/C200S/C205S/C138S/C164S
5.68
-
70C, pH 7.4, mutant enzyme C259S/C261S/C262S
6.24
-
70C, pH 7.4, mutant enzyme C259S/C261S/C262S/C200S/C205S/C138S
6.25
-
with 5'-methylthioadenosine as substrate
6.27
-
70C, pH 7.4, wild-type enzyme
6.35
-
purified enzyme
9.5
-
purified recombinant enzyme
10.2
-
purified enzyme
10.3
-
-
11.5
-
with 5'-methylthioadenosine as substrate
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.1 - 7.6
-
-
additional information
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 9
Caldariella acidophila
-
50% of activity maximum at pH 6.0 and pH 9.0
6.2 - 8.6
-
50% of activity maximum at pH 6.2 and pH 8.6
6.5 - 9
pH 6.5: about 55% of maximal activity, pH 9.0: about 55% of maximal activity
6.5 - 8.5
-
considerable decrease of activity below pH 6.5 and above pH 8.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
95
Caldariella acidophila
-
-
100
-
recombinant enzyme; recombinant enzyme
107
-
mutant enzyme C259S/C261S/C262S/C200S/C205S/C164S
112
-
mutant enzyme C259S/C261S/C262S/C200S/C205S
114
-
mutant enzyme C259S/C261S/C262S/C200S/C205S and mutant enzyme C259S/C261S/C262S
115
-
mutant enzyme C259S/C261S and mutant enzyme C259S
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 120
-
recombinant enzyme
60 - 120
-
60C: about 40% of maximal activity, 120C: about 40% of maximal activity, recombinant enzyme
86 - 95
90 - 130
-
90C: about 50% of maximal activity, 130C: about 70% of maximal activity
95 - 140
-
95C: about 50% of maximal activity, 140C: about 45% of maximal activity, wild-type enzyme
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7
-
isoelectric focusing on polyacrylamide gel in the pH ranges 3-10 and 4.5-6.0
6.54
-
calculation from nucleotide sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
MTAP is not detectable in 39% of chordomas
Manually annotated by BRENDA team
-
diffuse histiocytic lymphoma cell line, possesses no enzyme activity, but intact gene
Manually annotated by BRENDA team
-
highest level
Manually annotated by BRENDA team
-
and progenitor cells
Manually annotated by BRENDA team
-
cell line derived from metastases of malignant melanomas
Manually annotated by BRENDA team
-
tumor-derived cell line, bladder carcinoma
Manually annotated by BRENDA team
-
peripheral blood
Manually annotated by BRENDA team
-
diffuse, histiocytic
Manually annotated by BRENDA team
-
cell line derived from primary cutaneous melanoma
Manually annotated by BRENDA team
-
cell line derived from metastases of malignant melanomas
Manually annotated by BRENDA team
-
cell line derived from metastases of malignant melanomas
Manually annotated by BRENDA team
-
cell line derived from primary cutaneous melanoma
Manually annotated by BRENDA team
-
cell line derived from primary cutaneous melanoma; low content
Manually annotated by BRENDA team
-
cell line derived from primary cutaneous melanoma; low content
Manually annotated by BRENDA team
-
primary
Manually annotated by BRENDA team
-
SK-Ml-28 cell line derived from metastases of malignant melanomas
Manually annotated by BRENDA team
-
lung fibroblast cell line
Manually annotated by BRENDA team
-
decreased or no expression
Manually annotated by BRENDA team
-
CD34+ erythroid burst-forming unit, granulocyte/monocyte colony-forming unit, granulocyte/erythrocyte/macrophage/megakaryocyte colony-forming unit progenitors and primitive high proliferative potential colony-forming cells in the purified CD34+ cells are cultured
Manually annotated by BRENDA team
-
tumor-derived cell line, Burkitt's lymphoma
Manually annotated by BRENDA team
-
tumor-derived cell line, neuroblastoma
Manually annotated by BRENDA team
-
FC1010 skin fibroblast cell line
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
cytoplasmic MTAP is not detectable in 39% of chordomas
Manually annotated by BRENDA team
additional information
-
localized at the plasma membrane, in the cytoplasm and in the nucleus of transgenic tobacco plants. Abundant in the membrane structure and weak in the cytoplasm of onion epidermal cells
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Aeropyrum pernix (strain ATCC 700893 / DSM 11879 / JCM 9820 / NBRC 100138 / K1)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Sulfolobus solfataricus (strain ATCC 35092 / DSM 1617 / JCM 11322 / P2)
Sulfolobus solfataricus (strain ATCC 35092 / DSM 1617 / JCM 11322 / P2)
Sulfolobus tokodaii (strain DSM 16993 / JCM 10545 / NBRC 100140 / 7)
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27460
-
sequence analysis
28450
-
sequence analysis
54000
-
gel filtration
55000
-
gel filtration
64000
-
gel filtration
89000
-
gel filtration
160000
180000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 26000, calculated from sequence
hexamer
trimer
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in complex with adenine, by sitting- and hanging-drop formation at 22C, at 2.9 A resolution. Belongs to space group P3121, monomer consists of seven alpha-helices, ten beta-strands, and a 3(10)-helix. Residues between 216 and 225 demonstrate weak electron density for both subunits, therefore indicating this loop has high flexibility. Bound adenine is located in the deep pocket formed by the monomer with the entrance partially covered by the adjacent subunit. This flap is critical in the formation of a wide dimer interface
-
MTAN1 in its apo form and in complex with formycin A and 5'-methylthiotubercidin to a resolution of 2.0 A, 1.9 A and 1.8 A, respectively. By hanging-drop, vapor-diffusion technique. Belongs to space group P21. The monomer of MTAN1 has a mixed alpha/beta structure composed of a twisted, ten-stranded mixed beta sheet flanked by seven alpha helices and two short 3(10) helices. In the MTAN1 crystals, the asymmetric unit contains two monomers, which interact via an interface involving the four loops beta2-beta3, beta4-alpha2, beta6-alpha2b and beta8-alpha4, and the alpha2, alpha2b, and alpha5 helices. Both polar and apolar residues are involved in hydrogen bond and van der Waals interactions
-
the intersubunit interface of MTAN is highly hydrophobic and is dominated by van der Waals and hydrophobic interactions
-
crystal structures of apo MTAP and MTAP in complex with p-Cl-PhT-DADMe-ImmA are determined at 1.9 and 2.0 A resolution, respectively. Inhibitor binding causes condensation of the enzyme active site, reorganization at the trimer interfaces, the release of water from the active sites and subunit interfaces, and compaction of the trimeric structure. These structural changes cause the entropy-favored binding of transition state analogues
-
from recombinant enzyme, hanging drop-vapour diffusion method, protein 25 mg/ml, 10 mM Tris-HCl, pH 7.4, 5 mM DTT, 0.4 M NaCl against reservoir solution of 80 mM MES, pH 5.9, 5 mM DTT, 12% w/v polyethylene glycol 6000, 25% v/v ethylene glycol, in presence of substrates adenine, phosphate and sulfate, structure analysis by X-ray diffraction at light scattering
-
X-ray structure with (1S)-1-(9-deazaadenin-9-yl)-1,4-di-deoxy-1,4-imino-5-methylthio-D-ribitol
analysis of the crystal packing. Space group is C2, unit-cell parameters are a = 135.16, b = 138.09, c = 96.56 A, beta = 92.21. The asymmetric unit contains two independent half-hexamers, the other half of each of which is generated by a crystallographic twofold axis; the structure of SsMTAP II is originally determined in space group P1 and shows R32 pseudosymmetry. Post-analysis using phenix.xtriage shows that the correct space group is C2. The structure refined in space group C2 is reported and the factors that initially led to the incorrect space-group assignment are discussed
-
crystals are grown at either room temperature or 18C using the hanging drop vapor diffusion technique. Determination of the structure of 5'-deoxy-5'-methylthioadenosine phosphorylase alone, as ternary complexes with sulfate plus substrates 5'-deoxy-5'-methylthioadenosine, adenosine, or guanosine, or with the noncleavable substrate analog formycin B and as binary complexes with phosphate or sulfate alone. The structure of unliganded SsMTAP is refined at 2.5 A resolution and the structures of the complexes are refined at resolutions ranging from 1.6 A to 2.0 A
-
from recombinant enzyme, hanging drop-vapour diffusion method, protein solution, 7-10 mg/ml, 18C, reservoir solution for native crystals: Tris-HCl 10 mM, pH 7.4, 28-30% dioxane, 12% 2-methyl-2,4-pentanediol, 0.12 M MgCl2, 0,04 M NaCl, for crystals of enzyme complexed with substrates or sulfate and phosphate ions, substrates are added and NaCl is exchanged for MgSO4 or NH4Cl and KH2PO4, respectively, X-ray structure determination and analysis
-
hanging-drop, vapor-diffusion method at 22C, the crystal structure of the enzyme in complex with 5'-deoxy-5'-methylthioadenosine and sulfate is determined to 1.45 A resolution
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
4h, 40% loss of activity
37
4h, 90% loss of activity
40 - 55
-
15 min, stable
65
-
rapid inactivation
73
-
5 min, 50% residual activity, mutant enzyme C259S/C261S/C262S/C200S/C205S and mutant enzyme C259S/C261S/C262S/C200S/C205S/C138S/C164S
78
-
5 min, 50% residual activity, mutant enzyme C259S/C261S/C262S/C200S/C205S/C138S
91
-
5 min, 50% residual activity, mutant enzyme C259S/C261S/C262S
111
-
melting temperature of recombinant enzyme; recombinant enzyme, melting temperature
118
-
recombinant enzyme in presence of 100 mM phosphate, melting temperature
132
-
10 min, melting temperature
137
-
melting temperature
139
-
melting temperature in presence of 100 mM phosphate
145
-
half-life: 5 min
additional information
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
after 40 min exposure to 10.4 GHz microwave radiation at 90C the enzyme retains 78% activity compared to a control incubated at the same temperature without irradiation. KCl or NaCl increases the susceptibility to microwave irradiation. Protection against microwave inactivation by phosphate or sulfate.
-
dithiothreitol 0.8 M, reduction of thermostability
-
elimination of the disulfide bond Cys138Cys205 leads to an increased protease susceptibility
-
enzyme is extremely stable to proteolytic cleavage
-
no loss of activity after 24 h at room temperature in presence of 9 M urea, 4 M guanidine hydrochloride, 0.075% SDS, 50% methanol, 50% ethanol, 50% dimethylformamide, 1 M NaCl, and 1% Triton X-100
-
no loss of activity after treatment with thermolysin, trypsin, and chymotrypsin for 24 h at 37C
-
phosphate, and less efficiently also arsenate and sulfate, stabilize the recombinant enzyme against inactiviation by temperature, SDS, urea, and proteolytic enzymes
-
rapid inactivation in absence of reducing agents: 50% inactivation within 24 h at both 4C and -20C
-
recombinant enzyme, 90C in 2% SDS, 30 min, loss of 60% activity
-
recombinant enzyme, 90C in 8 M urea, 30 min, loss of 70% activity
-
resistance to thermal inactivation is increased remarkably by addition of 5'-methylthioadenosine or phosphate
-
Stable to freeze-thawing
-
transition midpoint for guanidinium chloride-induced unfolding is 3.0 M after 22 h incubation. The value decreases to 2.0 M in presence of 30 mM dithiothreitol. The guanidinium chloride-induced unfolding is completely reversible
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1-propanol
acetonitrile
dimethylformamide
Ethanol
guanidine-HCl
-
4 M, 24 h at room temperature, no loss of activity
Methanol
N,N-dimethylformamide
-
50%, 24 h at room temperature, no loss of activity
SDS
-
0.075%, 24 h at room temperature, no loss of activity. After 60 min of incubation in 2% SDS the enzyme remains fully active at 70C and retains 20% residual activity at 90C. Complete inactivation after 5 min at 100C in 0.5% SDS
tetrahydrofuran
Triton X-100
-
9 M, 24 h at room temperature, no loss of activity
urea
-
9 M, 24 h at room temperature, no loss of activity
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
O2 partially inactivates
-
637540
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 10 mM Tris-HC1, pH 7.4, containing 1 mM EDTA, stable for at least 1 year
-
-20C, 5 mM DTT, 50 mM potassium phosphate, pH 7.4, less than 10% loss of activity after 1 month
-
-20C, purified enzyme, Tris-HCl 10 mM, pH 7.4, 1 mM EDTA, stable at least 1 year
-
-20C, stable for at least 3 weeks
-
-20C, stable for several months
Caldariella acidophila
-
-70C, stable for at least 4 months
-
20C, Tris-HCl 10 mM, pH 7.4, purified enzyme, stable for at least 1 year
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
as a GST fusion form, by gel filtration
-
by centrifugation and on Ni-NTA column and by gel filtration; on Ni-NTA column
-
by ultrasonication, centrifugation, gel filtration and anion exchange chromatography, to homogeneity; by ultrasonication, centrifugation, gel filtration and anion exchange chromatography, to homogeneity
-
from lung; partial
-
Ni2+-Sepharose column chromatography
partial
recombinant enzyme
-
recombinant enzyme; recombinant from Escherichia coli
-
recombinant from Escherichia coli
recombinant His-tagged enzyme from Escherichia coli
-
using heat-treatment and MTA-Sepharose chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
different regions of MTAN cloned into the pGBT9.BS vector and transformed into Y190 yeast cells carrying pGAD.GH or pGAD.CBL3. Expressed in Escherichia coli BL21 cells carrying a GST fusion construct. MTAN promoter-GUS construct (pBI.tMTAN) transformed into Agrobacterium tumefaciens strain GV3101 and introduced into Arabidopsis plants by the floral dip method. 35S::CFP-CBL3-Myc and 35S::YFP-MTANHA constructs introduced, either alone or in combination, into Nicotiana benthamiana leaves by Agrobacterium tumefaciens-mediated infiltration method. CBL3-GFP and MTAN-GFP chimeric genes under the control of the cauliflower mosaic virus 35S promoter (pMD.CBL3 and pMD.MTAN) transiently expressed in Allium cepa epidermal cells. Onion epidermal cells bombarded with fusion constructs CBL3-YN and MTAN-YC
-
expressed in cutaneous squamous cell carcinoma cells
-
expressed in Drosophila melanogaster and Mus musculus
-
expressed in Escherichia coli
expressed in Escherichia coli BL21(DE3) cells
expression at a high level in Escherichia coli; overexpression in Escherichia coli strain RB791, amino acid determination, incorrect positioning of disulfide bonds, the recombinant enzyme is less thermostable and thermophilic than the native enzyme
-
expression in Escherichia coli
-
expression in Escherichichia coli
-
expression of His-tagged protein in Escherichia coli BL21(DE3) cells