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3.2.2.9: adenosylhomocysteine nucleosidase

This is an abbreviated version!
For detailed information about adenosylhomocysteine nucleosidase, go to the full flat file.

Word Map on EC 3.2.2.9

Reaction

5'-deoxyadenosine
+
H2O
=
5-deoxy-D-ribose
 +
adenine

Synonyms

(adoHcy)/methylthioadenosine nucleosidase, 5'-dAdo nucleosidase, 5'-deoxyadenosine/5'-methylthioadenosine nucleosidase, 5'-methyladenosine nucleosidase, 5'-methylthioadenosine nucleosidase, 5'-methylthioadenosine nucleosidases, 5'-methylthioadenosine/S-adenosylhomocysteine, 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase, 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase 2, 5-methylthioadenosine/S-adenosylhomocysteine nucleosidase, adenosylhomocysteine/methylthioadenosine nucleosidase, adoHcy/MeSAdo nucleosidase, adoHcy/MTA nucleosidase, Bgp, Bgp protein, BW246_00770, Cj0117, glycosaminoglycan-binding protein, K. pneumoniae MTA/SAH nucleosidase, methylthioadenosine nucleosidase, methylthioadenosine/S-adenosylhomocysteine nucleosidase, MKIGIIGA, MTA nucleosidase, MTA/AdoHcy nucleosidase, MTA/SAH nucleosidase, MTAN, Mtan-1, MTAN1, MTAN2, MTN1, MTN2, MtnN, nucleosidase, Pfs, Pfs protein, Pfs-2, Rv0091, S-adenosylhomocysteine nucleosidase, S-adenosylhomocysteine/5'-methylthioadenosine nucleosidase, SAHN

ECTree

     3 Hydrolases
         3.2 Glycosylases
             3.2.2 Hydrolysing N-glycosyl compounds
                3.2.2.9 adenosylhomocysteine nucleosidase

Inhibitors

Inhibitors on EC 3.2.2.9 - adenosylhomocysteine nucleosidase

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INHIBITOR
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]-3-hydroxy-4-phenylpyrrolidine
-
-
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine
-
-
(+/-)-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-cyclopentyl-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
-
-
(+/-)trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(3-methylphenylthio)-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(4-methylphenylthio)-D-ribitol
-
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol
(1S)-5-(4-chlorophenylthio)-1-(9-deaza-adenin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol
-
-
(2R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
(2R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(hydroxymethyl)sulfanyl]propan-1-ol
-
-
(2R,3R)-2-([[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]methyl)-4-(methylsulfanyl)butane-1,3-diol
(2R,3R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(2R,3S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(2R,3S)-4-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]-3-[(methylsulfanyl)methyl]butane-1,2-diol
(2S)-1-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-2-ol
(2S)-2-[[(1S)-1-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-hydroxyethyl]amino]-3-(methylsulfanyl)propan-1-ol
(2S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(hydroxymethyl)sulfanyl]propan-1-ol
-
-
(2S,3R)-1-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]-4-(methylsulfanyl)butane-2,3-diol
(2S,3R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(2S,3R)-N-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-3,4-dihydroxy-2-[(methylsulfanyl)methyl]butan-1-aminium trifluoroacetate
(2S,3S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-methylpyrrolidin-3-ol
most potent inhibitor tested, 5'-deoxyadenosine transition state analogue, dissociation constant of 640 pM. Inhibitor has a weak cell growth effect on Mycobacterium tuberculosis or Mycobacterium smegmatis but is lethal toward Helicobacter pylori
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol
-
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(hexylsulfanyl)methyl]pyrrolidin-3-ol
dissociation constant of 87 pM, inhibitor has a weak cell growth effect on Mycobacterium tuberculosis or Mycobacterium smegmatis but is lethal toward Helicobacter pylori
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)pyrrolidine
-
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine
(3R,4S)-4-(1-butylthiomethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
-
(3R,4S)-4-(4-chlorophenyl-thiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
potential antibiotic to interfere with the metabolic pathways involved in methylation, polyamine biosynthesis, methionine recycling, and quorum sensing pathways
(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)-butylthio-5'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin
-
-
(3R,4S)-ethylthio-5'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin
-
-
(3R,4S)-methylthio-5'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin
-
-
(4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(ethynylsulfanyl)methyl]pyrrolidin-3-ol
transition-state analogue, shows significant overlap in specificity with human 5'-methylthioadenosine phosphorylase MTAP
(4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(pent-4-yn-1-yl)sulfanyl]methyl]pyrrolidin-3-ol
transition-state analogue, best binding inhibitor tested, shows significant overlap in specificity with human 5'-methylthioadenosine phosphorylase MTAP
(5'R)-5'-deoxy-5'-methylthio-8,5'-cycloadenosine
-
competitive inhibition
(p-bromophenyl)thioadenosine
-
-
(p-fluorophenyl)thioadenosine
-
-
2',3'-didehydromethylthioadenosine
-
competitive inhibition
2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-2-[(methylsulfanyl)methyl]propane-1,3-diol
2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
3'-deoxy-methylthioadenosine
-
competitive inhibition
4-chlorophenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
5'-(2-ethylhex-1-yl)thio-DADMe-immucillin A
-
5'-(4-aminophenyl)thioadenosine
-
-
5'-(4-bromophenyl)thioadenosine
-
moderate inhibitor
5'-(4-chlorophenyl)thio-DADMe-immucillin A
-
5'-(4-chlorophenyl)thioadenosine
-
-
5'-(4-fluorophenyl)thioadenosine
-
moderate inhibitor
5'-(4-hydroxybutyl)thio-DADMe-immucillin A
-
5'-(4-iodophenyl)thioadenosine
-
-
5'-(4-nitrophenyl)thioadenosine
-
most potent inhibitor
5'-(p-nitrophenyl)thioadenosine
-
most potent inhibitor
5'-butylthio-DADMe-immucillin A
-
5'-butylthio-DADMe-ImmucillinA
-
potent MTAN inhibitor, disrupting autoinducer production in a dose-dependent manner without affecting growth. Despite having a 3fold lower affinity with purified MTAN, 5'-butylthio-DADMe-ImmucillinA inhibits cellular MTAN activity 5fold better than its methylthio- and ethylthio-counterparts, significant diffusion barrier
5'-butylthioadenosine
-
-
5'-Chloroadenosine
-
-
5'-Chloroformycin
5'-dimethylthioadenosine
-
-
5'-ethylthio-DADMe-ImmucillinA
-
potent MTAN inhibitor, disrupting autoinducer production in a dose-dependent manner without affecting growth
5'-ethylthioadenosine
5'-hexylthio-DADMe-immucillin A
most potent inhibitor
5'-isobutylthio-3-deaza-adenosine
-
poor inhibitor
5'-isobutylthioadenosine
-
-
5'-Isobutylthioinosine
-
-
5'-Isopropylthioadenosine
-
-
5'-Methylselenoadenosine
-
-
5'-methylthio-3-deaza-adenosine
-
poor inhibitor
5'-methylthio-DADMe-immucillin A
-
5'-methylthio-DADMe-ImmucillinA
-
potent MTAN inhibitor, disrupting autoinducer production in a dose-dependent manner without affecting growth
5'-methylthioadenosine
-
-
5'-Methylthioformycin
5'-methylthioinosine
-
-
5'-methylthiotubercidin
5'-n-butylthioinosine
-
-
5'-n-Propylthioadenosine
-
competitive inhibition
5'-p-aminophenylthioadenosine
-
Pfs protein shows 45% relative activity in the presence of 0.1 mM 5'-p-aminophenylthioadenosine, Bgp protein shows 20% relative activity in the presence of 0.1 mM 5'-p-aminophenylthioadenosine
5'-p-nitrophenylthioadenosine
-
-
5'-p-nitrophenythioadenosine
-
Pfs protein shows 0.6% relative activity in the presence of 0.1 mM 5'-p-aminophenylthioadenosine, Bgp protein shows 5% relative activity in the presence of 0.1 mM 5'-p-aminophenylthioadenosine
5'-phenylthioadenosine
-
moderate inhibitor
5'-propylthioadenosine
-
-
5'-purinothioadenosine
-
-
adenine
adenosine
-
-
benzylthio-immucillin A
-
-
butylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
picomolar inhibitor of MTAN
carbocyclic 5'-methylthioadenosine
-
-
ethylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
picomolar inhibitor of MTAN
ethylthio-immucillin A
-
-
ethylthio-immucillin-A
Formycin A
methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
methylthio-DADMe-immucillin-A
-
i.e. (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(methylsulfanyl)methyl]pyrrolidin-3-ol
methylthio-immucillin A
-
-
methylthio-immucillin-A
p-chlorophenylthio-immucillin A
-
-
p-tolylthio-immucillin-A
phenylthio-immucillin-A
S-8-aza-adenosyl-L-homocysteine
-
powerful inhibitor
S-8-aza-adenosylhomocysteine
-
-
S-adenosyl-L-homocysteine
-
moderate inhibitor
S-adenosyl-L-homocysteine sulfoxide
-
poor inhibitor
S-adenosylhomocysteine
-
competitive inhibition
S-formycinylhomocysteine
S-N6-dimethyl-3-deaza-adenosyl-L-homocysteine
-
poor inhibitor
S-Tubercidinylhomocysteine
-
powerful inhibitor
sinefungin
-
poor inhibitor
Tris
weak inhibitor; weak inhibitor, about 20% residual activity at 250 mM
additional information
-