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Literature summary for 5.4.99.9 extracted from

  • Kuppala, R.; Borrelli, S.; Slowski, K.; Sanders, D.A.; Ravindranathan Kartha, K.P.; Pinto, B.M.
    Synthesis and biological evaluation of nonionic substrate mimics of UDP-Galp as candidate inhibitors of UDP galactopyranose mutase (UGM) (2015), Bioorg. Med. Chem. Lett., 25, 1995-1997 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1-[5-O-(alpha-D-galactopyranosyl)-D-glucityl]pyrimidine-2,4(3H)-dione 28% enzyme inhibition at 0.5 mM Mycobacterium tuberculosis
1-[5-O-(beta-D-galactopyranosyl)-D-glucityl]pyrimidine-2,4(3H)-dione 30% enzyme inhibition at 0.5 mM Mycobacterium tuberculosis
additional information synthesis of 1-[5-O-(alpha-D-galactopyranosyl)-D-glucityl]pyrimidine-2,4(3H)-dione and 1-[5-O-(beta-D-galactopyranosyl)-D-glucityl]pyrimidine-2,4(3H)-dione as non-ionic substrate mimics of substrate UDP-alpha-D-galactopyranose. The nonionic polyhydroxylated chain is intended to mimic the ionic diphosphate group and the ribose moiety in UDP-Galp and to increase the bioavailabilities of the candidate inhibitors. Inhibition assays with UGM of Mycobacterium tuberculosis show only weak inhibition of the enzyme by the compounds. Retrosynthetic analysis of the target compounds, overview Mycobacterium tuberculosis

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
-
-
-

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
UDP galactopyranose mutase
-
Mycobacterium tuberculosis
UGM
-
Mycobacterium tuberculosis

Cofactor

Cofactor Comment Organism Structure
FAD
-
Mycobacterium tuberculosis

General Information

General Information Comment Organism
physiological function UDP-alpha-D-galactopyranose (UDP-Galp) is a precursor of galactofuranose (Galf), which is a primary component of the cell-wall glycans of several microorganisms. The interconversion of UDP-Galp and UDP-Galf is catalyzed by UDP galactopyranose mutase (UGM) Mycobacterium tuberculosis