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2.4.2.28: S-methyl-5'-thioadenosine phosphorylase

This is an abbreviated version!
For detailed information about S-methyl-5'-thioadenosine phosphorylase, go to the full flat file.

Word Map on EC 2.4.2.28

Reaction

S-methyl-5'-thioadenosine
+
phosphate
=
adenine
 +
S-methyl-5-thio-alpha-D-ribose 1-phosphate

Synonyms

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/S-adenosylhomocysteine nucleosidase, 5-methylthioadenosine phosphorylase, 5’-methylthioadenosine phosphorylase, MeSAdo phosphorylase, MeSAdo/Ado phosphorylase, methylthioadenosine nucleosidase, methylthioadenosine nucleoside phosphorylase, methylthioadenosine phosphorylase, MTA phosphorylase, MTAN, MTAN1, MTAN2, MTAP, Mtap protein, MTAPase, MTN1, MTN2, PfMTAP, phosphorylase, methylthioadenosine, RSFP, Rv0535, SsMTAP, SsMTAP II, SsMTAPII, SSO2343

ECTree

     2 Transferases
         2.4 Glycosyltransferases
             2.4.2 Pentosyltransferases
                2.4.2.28 S-methyl-5'-thioadenosine phosphorylase

Inhibitors

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

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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]-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
-
-
4-Cl-PhT-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin A
-
5'-(4-chlorophenyl)thio-DADMe-immucillin A
-
-
5'-butylthio-DADMe-immucillin A
-
-
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-Immucillin-A
-
5'-methylthio-DADMe-ImmucillinA
5'-methylthio-immucillin A
-
-
5'-methylthio-immucillin-adenine
-
i.e. MT-immucillin-A
5'-methylthiotubercidin
5'-n-Propylthioadenosine
-
-
5'-propylthio-DADMe-immucillin A
-
-
5-methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin A
-
5-methylthio-immucillin A
-
9-(phosphonoalkyl)adenine
-
-
9-(phosphonoheptyl)adenine
-
-
9-deazaadenine
-
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 37°C, phosphate protects
-
ribose 1-phosphate
-
-
S-adenosyl-L-homocysteine
SH-group blocking compounds
-
Subtilisin
-
recombinant enzyme, 24% remaining activity after 4 h at 37°C, 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
-