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Literature summary extracted from

  • Kincaid, V.A.; London, N.; Wangkanont, K.; Wesener, D.A.; Marcus, S.A.; Heroux, A.; Nedyalkova, L.; Talaat, A.M.; Forest, K.T.; Shoichet, B.K.; Kiessling, L.L.
    Virtual screening for UDP-galactopyranose mutase ligands identifies a new class of antimycobacterial agents (2015), ACS Chem. Biol., 10, 2209-2218 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
5.4.99.9 gene ugmA, recombinant expression in Escherichia coli strain BL21(DE3) Mycobacterium tuberculosis
5.4.99.9 gene ugmA, recombinant expression in Escherichia coli strain BL21(DE3) Klebsiella pneumoniae
5.4.99.9 gene ugmA, recombinant expression in Escherichia coli strain ER2523 Corynebacterium diphtheriae

Inhibitors

EC Number Inhibitors Comment Organism Structure
5.4.99.9 2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
 Caenorhabditis elegans
5.4.99.9 2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
 Corynebacterium diphtheriae
5.4.99.9 2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
 Klebsiella pneumoniae
5.4.99.9 2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
 Mycobacterium tuberculosis
5.4.99.9 2-(3-((4-chlorophenoxy)methyl)-6-(p-tolyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 97% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-((4-chlorophenoxy)methyl)-6-(p-tolyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 97% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-((4-chlorophenoxy)methyl)-6-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 95% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-((4-chlorophenoxy)methyl)-6-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 95% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(2-methylfuran-3-yl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 25% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(2-methylfuran-3-yl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 25% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(4-bromobenzyl)-6-(4-chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid
-
 Caenorhabditis elegans
5.4.99.9 2-(3-(4-bromobenzyl)-6-(4-chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid
-
 Corynebacterium diphtheriae
5.4.99.9 2-(3-(4-bromobenzyl)-6-(4-chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid second generation compound, competitive, 100% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(4-bromobenzyl)-6-(4-chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid second generation compound, competitive, 100% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(4-fluorobenzyl)-6-(p-tolyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 96% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(4-fluorobenzyl)-6-(p-tolyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 96% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(4-fluorobenzyl)-6-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 92% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(4-fluorobenzyl)-6-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 92% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(4-fluorobenzyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 92% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(4-fluorobenzyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 92% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(4-fluorophenyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 74% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(4-fluorophenyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 74% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(furan-2-yl)-6-(p-tolyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 62% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(furan-2-yl)-6-(p-tolyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 62% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(furan-2-yl)-6-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 46% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(furan-2-yl)-6-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 46% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-(furan-2-yl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 34% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-(furan-2-yl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 34% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(3-cyclopropyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 8.9% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(3-cyclopropyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 8.9% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(6-(4-chlorophenyl)-3-(2-methoxyphenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 91% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(6-(4-chlorophenyl)-3-(2-methoxyphenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 91% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(6-(4-chlorophenyl)-3-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 96% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(6-(4-chlorophenyl)-3-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 96% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(6-(4-chlorophenyl)-3-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid
-
 Caenorhabditis elegans
5.4.99.9 2-(6-(4-chlorophenyl)-3-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid
-
 Corynebacterium diphtheriae
5.4.99.9 2-(6-(4-chlorophenyl)-3-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid first generation compound, competitive, 95% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(6-(4-chlorophenyl)-3-(thiophen-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid first generation compound, competitive, 95% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(6-(4-chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 72% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(6-(4-chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 72% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 2-(6-(4-fluorophenyl)-3-(furan-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 38% inhibition at 0.1 mM Klebsiella pneumoniae
5.4.99.9 2-(6-(4-fluorophenyl)-3-(furan-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)acetic acid 38% inhibition at 0.1 mM Mycobacterium tuberculosis
5.4.99.9 3-(3-(2-(allylamino)thiazol-4-yl)-2,5-dimethyl-1H-pyrrol-1-yl)propanoic acid
-
 Klebsiella pneumoniae
5.4.99.9 3-(3-(2-(allylamino)thiazol-4-yl)-2,5-dimethyl-1H-pyrrol-1-yl)propanoic acid
-
 Mycobacterium tuberculosis
5.4.99.9 3-(6-(benzyloxy)-1H-indol-1-yl)propanoic acid
-
 Klebsiella pneumoniae
5.4.99.9 3-(6-(benzyloxy)-1H-indol-1-yl)propanoic acid
-
 Mycobacterium tuberculosis
5.4.99.9 additional information structure-based virtual screening for UDP-galactopyranose mutase ligands identifies a class of antimycobacterial agents, triazolothiadiazine inhibitors, using structures of UGMs from Aspergillus fumigatus, Trypanosoma cruzi, and Klebsiella pneumoniae (PDB ID 3INT) Caenorhabditis elegans
5.4.99.9 additional information structure-based virtual screening for UDP-galactopyranose mutase ligands identifies a class of antimycobacterial agents, triazolothiadiazine inhibitors, using structures of UGMs from Aspergillus fumigatus, Trypanosoma cruzi, and Klebsiella pneumoniae (PDB ID 3INT) Corynebacterium diphtheriae
5.4.99.9 additional information structure-based virtual screening for UDP-galactopyranose mutase ligands identifies a class of antimycobacterial agents, triazolothiadiazine inhibitors, using structures of UGMs from Aspergillus fumigatus, Trypanosoma cruzi, and Klebsiella pneumoniae (PDB ID 3INT) Klebsiella pneumoniae
5.4.99.9 additional information structure-based virtual screening for UDP-galactopyranose mutase ligands identifies a class of antimycobacterial agents, triazolothiadiazine inhibitors, using structures of UGMs from Aspergillus fumigatus, Trypanosoma cruzi, and Klebsiella pneumoniae (PDB ID 3INT) Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.4.99.9 UDP-alpha-D-galactopyranose Caenorhabditis elegans
-
 UDP-alpha-D-galactofuranose
-
 r
5.4.99.9 UDP-alpha-D-galactopyranose Mycobacterium tuberculosis
-
 UDP-alpha-D-galactofuranose
-
 r
5.4.99.9 UDP-alpha-D-galactopyranose Klebsiella pneumoniae
-
 UDP-alpha-D-galactofuranose
-
 r
5.4.99.9 UDP-alpha-D-galactopyranose Corynebacterium diphtheriae
-
 UDP-alpha-D-galactofuranose
-
 r

Organism

EC Number Organism UniProt Comment Textmining
5.4.99.9 Caenorhabditis elegans
-
-
-
5.4.99.9 Corynebacterium diphtheriae Q6NER4
-
-
5.4.99.9 Klebsiella pneumoniae Q48485
-
-
5.4.99.9 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.4.99.9 UDP-alpha-D-galactopyranose
-
 Caenorhabditis elegans UDP-alpha-D-galactofuranose
-
 r
5.4.99.9 UDP-alpha-D-galactopyranose
-
 Mycobacterium tuberculosis UDP-alpha-D-galactofuranose
-
 r
5.4.99.9 UDP-alpha-D-galactopyranose
-
 Klebsiella pneumoniae UDP-alpha-D-galactofuranose
-
 r
5.4.99.9 UDP-alpha-D-galactopyranose
-
 Corynebacterium diphtheriae UDP-alpha-D-galactofuranose
-
 r

Synonyms

EC Number Synonyms Comment Organism
5.4.99.9 Glf
-
 Caenorhabditis elegans
5.4.99.9 Glf
-
 Mycobacterium tuberculosis
5.4.99.9 Glf
-
 Klebsiella pneumoniae
5.4.99.9 Glf
-
 Corynebacterium diphtheriae
5.4.99.9 UGM
-
 Caenorhabditis elegans
5.4.99.9 UGM
-
 Mycobacterium tuberculosis
5.4.99.9 UGM
-
 Klebsiella pneumoniae
5.4.99.9 UGM
-
 Corynebacterium diphtheriae
5.4.99.9 uridine 5'-diphosphate-galactopyranose mutase
-
 Caenorhabditis elegans
5.4.99.9 uridine 5'-diphosphate-galactopyranose mutase
-
 Mycobacterium tuberculosis
5.4.99.9 uridine 5'-diphosphate-galactopyranose mutase
-
 Klebsiella pneumoniae
5.4.99.9 uridine 5'-diphosphate-galactopyranose mutase
-
 Corynebacterium diphtheriae

Cofactor

EC Number Cofactor Comment Organism Structure
5.4.99.9 FAD enzyme UGM possesses a flavin adenine dinucleotide (FAD) cofactor that it uses to catalyze ring contraction of UDP-galactopyranose (UDP-Galp) to form UDP-galactofuranose (UDP-Galf) Caenorhabditis elegans
5.4.99.9 FAD enzyme UGM possesses a flavin adenine dinucleotide (FAD) cofactor that it uses to catalyze ring contraction of UDP-galactopyranose (UDP-Galp) to form UDP-galactofuranose (UDP-Galf) Mycobacterium tuberculosis
5.4.99.9 FAD enzyme UGM possesses a flavin adenine dinucleotide (FAD) cofactor that it uses to catalyze ring contraction of UDP-galactopyranose (UDP-Galp) to form UDP-galactofuranose (UDP-Galf) Klebsiella pneumoniae
5.4.99.9 FAD enzyme UGM possesses a flavin adenine dinucleotide (FAD) cofactor that it uses to catalyze ring contraction of UDP-galactopyranose (UDP-Galp) to form UDP-galactofuranose (UDP-Galf) Corynebacterium diphtheriae

General Information

EC Number General Information Comment Organism
5.4.99.9 evolution all organisms that generate Galf-containing glycans encode a UGM homologue Caenorhabditis elegans
5.4.99.9 evolution all organisms that generate Galf-containing glycans encode a UGM homologue Mycobacterium tuberculosis
5.4.99.9 evolution all organisms that generate Galf-containing glycans encode a UGM homologue Klebsiella pneumoniae
5.4.99.9 evolution all organisms that generate Galf-containing glycans encode a UGM homologue Corynebacterium diphtheriae
5.4.99.9 physiological function the enzyme catalyzes the formation of UDP-galactofuranose (UDP-Galf), which is required to produce Galf-containing glycoconjugates Caenorhabditis elegans
5.4.99.9 physiological function the enzyme catalyzes the formation of UDP-galactofuranose (UDP-Galf), which is required to produce Galf-containing glycoconjugates Mycobacterium tuberculosis
5.4.99.9 physiological function the enzyme catalyzes the formation of UDP-galactofuranose (UDP-Galf), which is required to produce Galf-containing glycoconjugates Klebsiella pneumoniae
5.4.99.9 physiological function the enzyme catalyzes the formation of UDP-galactofuranose (UDP-Galf), which is required to produce Galf-containing glycoconjugates Corynebacterium diphtheriae