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Literature summary for 3.2.2.9 extracted from

  • Longshaw, A.I.; Adanitsch, F.; Gutierrez, J.A.; Evans, G.B.; Tyler, P.C.; Schramm, V.L.
    Design and synthesis of potent sulfur-free transition state analogue inhibitors of 5'-methylthioadenosine nucleosidase and 5'-methylthioadenosine phosphorylase (2010), J. Med. Chem., 53, 6730-6746.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.2.2.9

Inhibitors

Inhibitors Comment Organism Structure
(+/-)-cis-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(1H-1,2,3-triazol-4-yl)pyrrolidine
-
 Escherichia coli
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(penta-3-yl)pyrrolidine
-
 Escherichia coli
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-isobutylpyrrolidine
-
 Escherichia coli
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-phenylpyrrolidine
-
 Escherichia coli
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine
-
 Escherichia coli
(+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethynyl-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-(cyclohexylmethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-allyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-cyclopentyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-cyclopropyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)-trans-4-[3-(benzylthio)propyl]-1-[(9-deazaadenin-9-yl)-methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(+/-)trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
 Escherichia coli
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine
-
 Escherichia coli
(3R,4S)-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
 Escherichia coli
(3R,4S)-butylthio-5'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin
-
 Escherichia coli
(3R,4S)-ethylthio-5'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin
-
 Escherichia coli
(3R,4S)-methylthio-5'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin
-
 Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5'-methylthioadenosine + H2O Escherichia coli
-
 5-methylthio-D-ribose + adenine
-
 ?
S-adenosyl-L-homocysteine + H2O Escherichia coli
-
 S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Purification (Commentary)

Purification (Comment) Organism
Ni-NTA column chromatography Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5'-methylthioadenosine + H2O
-
 Escherichia coli 5-methylthio-D-ribose + adenine
-
 ?
S-adenosyl-L-homocysteine + H2O
-
 Escherichia coli S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
 ?

Synonyms

Synonyms Comment Organism
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase dual substrate enzyme Escherichia coli
MTAN
-
 Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000034
-
 (3R,4S)-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000009
-
 (+/-)-trans-4-butyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000013
-
 (+/-)-trans-4-cyclopentyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.00003
-
 (+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-phenylpyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000047
-
 (+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-isobutylpyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000054
-
 (+/-)-trans-4-[3-(benzylthio)propyl]-1-[(9-deazaadenin-9-yl)-methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000059
-
 (+/-)-trans-4-(cyclohexylmethyl)-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000063
-
 (+/-)-trans-4-cyclopropyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.000064
-
 (+/-)-trans-4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.00031
-
 (3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.00035
-
 (+/-)-trans-4-allyl-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.00039
-
 (+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethynyl-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.00065
-
 (+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.0007
-
 (+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(penta-3-yl)pyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.00084
-
 (+/-)trans-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.0018
-
 (+/-)-cis-1-[(9-deazaadenin-9-yl)methyl]-4-ethyl-3-hydroxypyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli
0.002
-
 (+/-)-trans-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(1H-1,2,3-triazol-4-yl)pyrrolidine in 100 mM HEPES, pH 7.4, 50 mM KCl, at 25°C Escherichia coli