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Literature summary for 5.4.99.9 extracted from

  • Mahdavi-Amiri, Y.; Mohan, S.; Borrelli, S.; Slowski, K.; Sanders, D.A.; Pinto, B.M.
    Mechanism-based candidate inhibitors of uridine diphosphate galactopyranose mutase (UGM) (2016), Carbohydr. Res., 419, 1-7 .
    View publication on PubMed
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Inhibitors

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

Localization Comment Organism GeneOntology No. Textmining

Natural Substrates/ Products (Substrates)

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

Organism UniProt Comment Textmining
Mycobacterium tuberculosis
-
-
-

Reaction

Reaction Comment Organism Reaction ID
UDP-alpha-D-galactopyranose = UDP-alpha-D-galactofuranose detailed reaction mechanism involving SN2-type steps, overview Mycobacterium tuberculosis
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
UDP-alpha-D-galactopyranose
-
 Mycobacterium tuberculosis UDP-alpha-D-galactofuranose
-
 r

Synonyms

Synonyms Comment Organism
UGM
-
 Mycobacterium tuberculosis
uridine diphosphate galactopyranose mutase
-
 Mycobacterium tuberculosis

Cofactor

Cofactor Comment Organism Structure
FAD
-
 Mycobacterium tuberculosis

General Information

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