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Information on EC 2.4.2.28 - S-methyl-5'-thioadenosine phosphorylase
for references in articles please use BRENDA:EC2.4.2.28
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EC Tree 2 Transferases
2.4 Glycosyltransferases
2.4.2 Pentosyltransferases
2.4.2.28 S-methyl-5'-thioadenosine phosphorylase
IUBMB Comments
Also acts on 5′-deoxyadenosine and other analogues having 5′-deoxy groups.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
- 2.4.2.28
- purine
- polyamine
-
salvage
-
mtap-deficient
-
cdkn2a
- mesothelioma
-
phosphorolysis
-
mesothelial
- nucleosidase
-
codeleted
-
l-alanosine
-
co-deletion
-
mtap-deleted
-
phosphorylase-deficient
- p15ink4b
- 5'-deoxyadenosine
- 5-methylthioribose
-
mtans
-
p14arf
-
enzyme-deficient
- diagnostics
- drug development
- medicine
- analysis
Reaction Schemes
showSynonyms
methylthioadenosine phosphorylase, 5'-methylthioadenosine phosphorylase, mta phosphorylase, mtap protein, 5'-deoxy-5'-methylthioadenosine phosphorylase, ssmtapii, ssmtap, mtapase, mesado phosphorylase, pfmtap, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
5'-deoxy-5'-methylthioadenosine phosphorylase
5'-deoxy-5'-methylthioadenosine phosphorylase II
5'-deoxy-5'-methylthioadenosine:orthophosphate methylthioribosyltransferase
5'-methylthioadenosine nucleosidase
5'-methylthioadenosine phosphorylase
5-methylthioadenosine phosphorylase
MeSAdo phosphorylase
-
-
-
-
MeSAdo/Ado phosphorylase
-
-
-
-
methylthioadenosine nucleoside phosphorylase
-
-
-
-
methylthioadenosine phosphorylase
MTA phosphorylase
MTAN
MTAP
MTAPase
-
-
-
-
phosphorylase, methylthioadenosine
-
-
-
-
SsMTAP II
SsMTAPII
SSO2343
5'-deoxy-5'-methylthioadenosine phosphorylase
-
-
-
-
5'-deoxy-5'-methylthioadenosine phosphorylase II
-
5'-deoxy-5'-methylthioadenosine:orthophosphate methylthioribosyltransferase
-
5'-methylthioadenosine nucleosidase
-
-
-
-
5'-methylthioadenosine phosphorylase
-
-
-
-
methylthioadenosine phosphorylase
-
-
-
-
methylthioadenosine phosphorylase
-
-
MTA phosphorylase
-
-
-
-
MTAP
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
sequential mechanism
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S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
sequential mechanism
Caldariella acidophila
-
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
catalytic mechanism
-
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
catalytic mechanism
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
active and substrate-binding sites, three-dimensional structures
-
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
active and substrate-binding sites, three-dimensional structures
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
phosphorolytic mechanism
-
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
phosphorolytic mechanism
-
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
phosphorolytic mechanism
Caldariella acidophila
-
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
ordered bisubstrate biproduct reaction with methylthioadenosine the first substrate to add and adenine the last product to leave the enzyme
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S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
equilibrium-ordered reaction, 5'-methylthioadenosine is the first substrate to bind and 5-methylthioribose 1-phosphate is the first product to be released
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S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
subunit structure, model
S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
3 binding sites between substrate and enzyme
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S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
transition state structure, computational modeling of the transition state, overview
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S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pentosyl group transfer
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-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
5'-deoxyadenosine degradation I, S-methyl-5'-thioadenosine degradation II
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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.
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CAS REGISTRY NUMBER
COMMENTARY
61970-06-7
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2',3'-dideoxyadenosine + phosphate
adenine + 2,3-deoxy-D-ribose 1-phosphate
-
Substrates: substrate for trypanosomal but not for mammalian enzyme
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2'-chloro-2'-deoxyadenosine + phosphate
adenine + 2-chloro-2-deoxy-alpha-D-ribose 1-phosphate
2'-deoxy-2'-amino-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-2-amino-5-thio-D-ribose 1-phosphate
-
Substrates: -
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2'-deoxy-2'-azido-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-2-azido-5-thio-D-ribose 1-phosphate
-
Substrates: -
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2'-deoxy-2-fluoro-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-2-fluoro-5-thio-D-ribose 1-phosphate
-
Substrates: -
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2'-deoxy-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 2-deoxy-5-thio-D-ribose 1-phosphate
-
Substrates: -
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2'-deoxyadenosine + phosphate
adenine + 2'-deoxy-D-ribose 1-phosphate
Substrates: the enzyme can use adenosine with the same efficiency as 5'-deoxy-5'-methylthioadenosine
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?
2-amino-5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
2-aminoadenosine + 5-hydroxyethylthio-D-ribose 1-phosphate
-
Substrates: 28% activity compared to 5'-methyladenosine or 5'-deoxy-5'-(hydroxyethylthio)adenosine
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2-chloro-2'-deoxyadenosine + phosphate
2-chloroadenine + 2-deoxy-D-ribose 1-phosphate
-
Substrates: -
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r
2-chloro-5'-O-methyl-2'-deoxyadenosine + phosphate
2-chloroadenine + 5-O-methyl-2-deoxy-D-ribose 1-phosphate
-
Substrates: -
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r
2-chloroadenosine + phosphate
2-chloroadenine + D-ribose 1-phosphate
-
Substrates: -
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r
2-fluoro-5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
2-fluoroadenosine + 5-hydroxyethylthio-D-ribose 1-phosphate
-
Substrates: 149% activity compared to 5'-methyladenosine or 5'-deoxy-5'-(hydroxyethylthio)adenosine
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3'-deoxy-5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 3-deoxy-5-thio-D-ribose 1-phosphate
-
Substrates: -
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?
3'-deoxyadenosine + phosphate
adenine + 3-deoxy-D-ribose 1-phosphate
-
Substrates: substrate for trypanosomal but not for mammalian enzyme
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5'-deoxy-5'-(1,3-thiazol)-2-yl-sulfanyladenosine + phosphate
adenine + 5-(1,3-thiazol-2-yl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(2-(pyridin-2-yl)ethyl)-thioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(2-methylbutyl)-thioadenosine + phosphate
adenine + 5-(2-methylbutyl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(2-methylphenyl)-thioadenosine + phosphate
adenine + 5-(2-methylphenyl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(3-methylphenyl)-thioadenosine + phosphate
adenine + 5-(3-methylphenyl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(4-methoxyphenyl)-thioadenosine + phosphate
adenine + 5-(4-methoxyphenyl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(4-methylphenyl)-thioadenosine + phosphate
adenine + 5-(4-methylphenyl)thio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
adenine + 5-hydroxyethylthio-D-ribose 1-phosphate
5'-deoxy-5'-(phenylethyl)-thioadenosine + phosphate
adenine + 5-phenylethylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(phenylmethyl)-thioadenosine + phosphate
adenine + 5-phenylmethylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-(quinolin-2-yl)-sulfanyladenosine + phosphate
adenine + 5-(quinolin-2-yl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-butylthioadenosine + phosphate
adenine + 5-butylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-cyclohexyl-thioadenosine + phosphate
adenine + 5-cyclohexylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-cyclopentyl-thioadenosine + phosphate
adenine + 5-cyclopentylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-hydroxyethylthioadenosine + phosphate
adenine + 5-(2-hydroxyethyl)thio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-imidazol-2-yl-sulfanyladenosine + phosphate
adenine + 5-(imidazol-2-yl)thio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-isobutylthioadenosine + phosphate
adenine + 5-isobutylthio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-isopentylthioadenosine + phosphate
adenine + 5-isopentylthio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-methyl-thioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5'-deoxy-5'-methyl-thio-D-ribose-1-phosphate
Substrates: -
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5'-deoxy-5'-phenyl-thioadenosine + phosphate
adenine + 5-phenylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-phenylmethylene-adenosine + phosphate
adenine + 5-deoxy-5-phenylmethylene-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-pyridin-2-yl-sulfanyladenosine + phosphate
adenine + 5-(pyridin-2-yl)thio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-pyridin-4-yl-sulfanyladenosine + phosphate
adenine + 5-(pyridin-4-yl)thio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-tert-butylthioadenosine + phosphate
adenine + 5-tert-butylthio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'-[4-(trifluoromethyl)phenyl]-thioadenosine + phosphate
adenine + 5-[4-(trifluoromethyl)phenyl]thio-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-5'phenylaminoadenosine + phosphate
adenine + 5-deoxy-5-phenylamino-D-ribose 1-phosphate
-
Substrates: -
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?
5'-deoxy-adenosine + phosphate
adenine + 5-thio-D-ribose 1 phosphate
-
Substrates: -
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?
5'-iodo-5'-deoxyadenosine + phosphate
adenine + 5-iodo-5-deoxy-D-ribose 1-phosphate
-
Substrates: -
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r
5'-isobutylthioinosine + phosphate
hypoxanthine + 5-isobutylthio-D-ribose 1-phosphate
Caldariella acidophila
-
Substrates: 8.1% of the reaction with 5'-methylthioadenosine
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5'-methylselenoadenosine + phosphate
adenine + 5-methylseleno-D-ribose 1-phosphate
-
Substrates: 95% of the activity with 5'-methylthioadenosine
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?
5'-methylthioadenosine + phosphate
adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
Substrates: -
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?
5'-n-butylthioadenosine + phosphate
adenine + 5-n-butylthio-D-ribose 1-phosphate
Caldariella acidophila
-
Substrates: 93.3% of the reaction with 5'-methylthioadenosine
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5'-n-propylthioadenosine + phosphate
adenine + 5-n-propylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-phenyladenosine + phosphate
adenine + 5-phenyl-D-ribose 1-phosphate
-
Substrates: -
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6-methylpurine 2'-deoxyribonucleoside + phosphate
6-methylpurine + 2-deoxy-D-ribose 1-phosphate
-
Substrates: substrate for trypanosomal but not for mammalian enzyme
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?
9-[2-deoxy-beta-D-ribofuranosyl]-6-methylpurine + phosphate
?
-
Substrates: a toxic prodrug, 5% of the activity with S-methyl-5'-thioadenosine
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9-[6-deoxy-beta-L-talofuranosyl]-2-F-adenine + phosphate
?
-
Substrates: a toxic prodrug, 23% of the activity with S-methyl-5'-thioadenosine
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deoxyadenosine + phosphate
adenine + deoxy-D-ribose 1-phosphate
-
Substrates: -
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S-adenosyl-L-homocysteine + phosphate
?
Substrates: 0.81% activity compared to activity with 5'-methylthioadenosine
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S-adenosylhomocysteine + phosphate
?
Substrates: 14% relative activity
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S-methyl-5'-thioadenosine + arsenate
adenine + S-methyl-5-thio-alpha-D-ribose 1-arsenate
-
Substrates: arsenolysis
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S-methyl-5'-thioadenosine + phosphate
adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
2'-chloro-2'-deoxyadenosine + phosphate
adenine + 2-chloro-2-deoxy-alpha-D-ribose 1-phosphate
-
Substrates: -
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?
2'-chloro-2'-deoxyadenosine + phosphate
adenine + 2-chloro-2-deoxy-alpha-D-ribose 1-phosphate
-
Substrates: -
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?
2'-deoxyadenosine + phosphate
adenine + 2-deoxy-D-ribose 1-phosphate
-
Substrates: low activity
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r
2'-deoxyadenosine + phosphate
adenine + 2-deoxy-D-ribose 1-phosphate
-
Substrates: -
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2'-deoxyadenosine + phosphate
adenine + 2-deoxy-D-ribose 1-phosphate
-
Substrates: substrate for trypanosomal but not for mammalian enzyme
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2'-fluoro-2'-deoxyadenosine + phosphate
adenine + 2'-fluoro-2'-deoxy-D-ribose 1-phosphate
-
Substrates: -
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2'-fluoro-2'-deoxyadenosine + phosphate
adenine + 2'-fluoro-2'-deoxy-D-ribose 1-phosphate
-
Substrates: -
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5'-butylthioadenosine + phosphate
adenine + 5-butylthio-D-ribose 1-phosphate
Substrates: 24% relative activity
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5'-butylthioadenosine + phosphate
adenine + 5-butylthio-D-ribose 1-phosphate
Substrates: 25% relative activity
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5'-chloroadenosine + phosphate
adenine + 5-deoxy-5-chloro-D-ribose 1-phosphate
Substrates: 13% relative activity
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5'-chloroadenosine + phosphate
adenine + 5-deoxy-5-chloro-D-ribose 1-phosphate
Substrates: 4% relative activity
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5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
adenine + 5-hydroxyethylthio-D-ribose 1-phosphate
-
Substrates: trypanocidal substrate analogue
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5'-deoxy-5'-(hydroxyethylthio)adenosine + phosphate
adenine + 5-hydroxyethylthio-D-ribose 1-phosphate
-
Substrates: preincubation of cells with the substrate lead to 22-37% inhibition of spermidine synthesis from ornithine and 2-7fold increased cytosolic levels of S-adenosyl-L-methionine and S-adenosyl-L-homocysteine, and up to 8fold increased cytosolic level of 5'-methyladenosine
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: sugar specificity
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: salvage reaction
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: involved in cardiac purine breakdown during ischemia
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: substrate is a by-product of polyamine biosynthesis, which is essential for cell growth and proliferation
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: substrate-induced conformational change involving Glu163, which is located at the interface between subunits and swings in toward the active site upon nucleoside binding
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: the transition state is stabilized in different ways for 6-amino versus 6-oxo substrates
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-deoxy-5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxyadenosine + phosphate
adenine + 5-deoxy-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxyadenosine + phosphate
adenine + 5-deoxy-D-ribose 1-phosphate
-
Substrates: -
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5'-deoxyadenosine + phosphate
adenine + 5-deoxy-D-ribose 1-phosphate
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Substrates: -
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5'-deoxyadenosine + phosphate
adenine + 5-deoxy-D-ribose 1-phosphate
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Substrates: phosphate-dependent
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5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
Substrates: 40% relative activity
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5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
Substrates: 42% relative activity
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5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
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Substrates: 60% of the activity with 5'-methylthioadenosine
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5'-ethylthioadenosine + phosphate
adenine + 5-ethylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-iodoadenosine + phosphate
adenine + 5-deoxy-5-iodo-D-ribose 1-phosphate
Substrates: 17% relative activity
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5'-iodoadenosine + phosphate
adenine + 5-deoxy-5-iodo-D-ribose 1-phosphate
Substrates: 28% relative activity
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5'-isobutylthioadenosine + phosphate
adenine + 5-isobutylthio-D-ribose 1-phosphate
Substrates: 32% relative activity
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5'-isobutylthioadenosine + phosphate
adenine + 5-isobutylthio-D-ribose 1-phosphate
Substrates: 17% relative activity
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5'-isobutylthioadenosine + phosphate
adenine + 5-isobutylthio-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: 97% of the reaction with 5'-methylthioadenosine
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: 100% relative activity
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: adenine-bound MTAN1 is exclusively in its closed form, substantial conformational changes occur in this region during the enzymatic reaction. Residues Met35, Val90, Leu181, Met201, Phe237 and Ile143', Ile145' and Phe148' in a neighboring MTAN1 monomer bind adenine via hydrophobic and van der Waals interactions. The hydrophobic side chains Phe237 and Leu181 show structural perturbations that provide the flexible accommodation of the adenine ring. The carboxylic side chain of Asp225 hydrogen bonds with nitrogen atoms in the adenine ring, therefore being key determinant for the adenine base. The side chain Thr116 and backbone Gly118 also interact with the adenine molecule
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: hydrolysis of 5'-methylthioadenosine predominates despite MTAN2 possessing both 5'-methylthioadenosine and S-adenosylhomocysteine hydrolysis activity. MTAN2 binds 5'-methylthioadenosine approximately 6fold higher than S-adenosylhomocysteine. Residues between 216 and 225 in MTAN2 contain conformational differences representing an open conformation when compared with MTAN1. The side chains Met22, Val78, Met168, Met188, Phe224 along with Ile130', Val132' and Leu135' in a neighboring MTAN2 monomer bind adenine via hydrophobic and van der Waals interactions. The hydrophobic side chains Phe224 and Met168 show structural perturbations that provide the flexible accommodation of the adenine ring. The carboxylic side chain of Asp211 hydrogen bonds with nitrogen atoms in the adenine ring, therefore being key determinant for the adenine base. The side chain Thr103 and backbone Gly105 also interact with the adenine molecule
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: an antiproliferative effect on stimulated human lymphocytes and virally transformed mouse fibroblasts
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: involved in salvage of adenine and methionine from 5'-methylthioadenosine
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: physiological significance of 5'-methylthioadenosine cleavage is probably related to removal of the thioether which in turn exerts a significant inhibition on methyl transfer reactions
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: completely dependent on phosphate
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: important for the salvage of adenine and methionine
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: involved in salvage of adenine and methionine from 5'-methylthioadenosine
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: structural comparison of MTA phosphorylase and MTA/AdoHcy nucleosidase explains substrate preferences and identifies regions exploitable for inhibitor design
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: 5'-methylthioadenosine is the best substrate
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: preferred direction of reaction is temperature-dependent
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: involved in salvage of adenine and methionine from 5'-methylthioadenosine
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: completely dependent on phosphate
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: binding of phosphate and 5-methylthioribose 1-phosphate to the enzyme induces a conformational transition that stabilizes the folded structure of the enzyme
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: 5'-methylthioadenosine and adenine form ternary complexes with the enzyme only in presence of phosphate and methylthioribose 1-phosphate, respectively
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: the enzyme regulates ornithine decarboxylase by production of downstream metabolites. Tumor suppressor activity of MTAP may be due to its effect on ornithine decarboxylase activity
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: the [3'-2H] kinetic isotope effect is consistent with a unique H3'-endo-exo configuration and 3'-hydroxyl polarization without full ionization at the MTAN transition state. The MTAN transition state is a fully dissociative (SN1), ribooxacarbenium-like structure with its C1'-N9 distance larger than 3.2 A. The ribosyl moiety adopts a H3'-endo-exo transition conformation, and the 3'-OH residue is partially polarized by the adjacent carboxylate with a hydrogen bond distance of 2.83 A. The MTAN transition state has a geometry between the unrestrained H3'-endo 5'-methylthioadenosine substrate and a fully developed 3'-exo ribooxacarbenium ion
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
-
Substrates: -
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5'-methylthioadenosine + phosphate
adenine + 5-methylthio-D-ribose 1-phosphate
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Substrates: completely dependent on phosphate
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5'-methylthioinosine + phosphate
hypoxanthine + 5-methylthio-alpha-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: -
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5'-methylthioinosine + phosphate
hypoxanthine + 5-methylthio-alpha-D-ribose 1-phosphate
Caldariella acidophila
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Substrates: 8.8% of the reaction with 5'-methylthioadenosine
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5'-methylthioinosine + phosphate
hypoxanthine + 5-methylthio-alpha-D-ribose 1-phosphate
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Substrates: 8.9% of the reaction with 5'-methylthioadenosine
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5'-phenylthioadenosine + phosphate
adenine + 5-phenylthio-D-ribose 1-phosphate
Substrates: 39% relative activity
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5'-phenylthioadenosine + phosphate
adenine + 5-phenylthio-D-ribose 1-phosphate
Substrates: 12% relative activity
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adenosine + phosphate
adenine + D-ribose 1-phosphate
Substrates: 6% relative activity
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
Substrates: 2.1% activity compared to activity with 5'-methylthioadenosine
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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adenosine + phosphate
adenine + D-ribose 1-phosphate
-
Substrates: -
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