Inhibitors | Comment | Organism | Structure |
---|---|---|---|
(2S)-2-deoxy-2-selenonium-2-[(2S,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexyl]-D-arabinitol chloride | a transition-state analogue, shows about 25% inhibition at 0.5 mm | Mycobacterium tuberculosis | |
(2S)-2-deoxy-2-sulfonium-2-[(2S,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexyl]-D-arabinitol chloride | a transition-state analogue, shows about 25% inhibition at 0.5 mm | Mycobacterium tuberculosis | |
additional information | synthesis of a sulfonium and selenonium ion with an appended polyhydroxylated side chain. The compounds are designed as transition state mimics of the UGM-catalyzed reaction, where the head groups carrying a permanent positive charge, and are designed to mimic both the shape and positive charge of the proposed galactopyranosyl cation-like transition state, HPLC-based UGM inhibition assay. Even modifying one of these inhibitors by attaching the uridine monophosphate (UMP) fragment via an alpha-linkage to the 1,4-dideoxy-1,4-imino-D-galctitol moiety using a three-carbon linker does not improve the inhibitory profile significantly. Retrosynthetic inhibitor analysis, detailed overview | Mycobacterium tuberculosis |
Localization | Comment | Organism | GeneOntology No. | Textmining |
---|
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
UDP-alpha-D-galactopyranose | Mycobacterium tuberculosis | - |
UDP-alpha-D-galactofuranose | - |
r |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Mycobacterium tuberculosis | - |
- |
- |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
UDP-alpha-D-galactopyranose = UDP-alpha-D-galactofuranose | detailed reaction mechanism involving SN2-type steps, overview | Mycobacterium tuberculosis |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
UDP-alpha-D-galactopyranose | - |
Mycobacterium tuberculosis | UDP-alpha-D-galactofuranose | - |
r |
Synonyms | Comment | Organism |
---|---|---|
UGM | - |
Mycobacterium tuberculosis |
uridine diphosphate galactopyranose mutase | - |
Mycobacterium tuberculosis |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
FAD | - |
Mycobacterium tuberculosis |
General Information | Comment | Organism |
---|---|---|
physiological function | UDP-galactopyranose mutase (UGM), an enzyme found in many eukaryotic and prokaryotic human pathogens, catalyzes the interconversion of UDP-galactopyranose (UDP-Galp) and UDPgalactofuranose (UDP-Galf), the latter being used as the biosynthetic precursor of the galactofuranose polymer portion of the mycobacterium cell wall | Mycobacterium tuberculosis |