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Literature summary for 5.4.99.9 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)

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

Inhibitors

Inhibitors Comment Organism Structure
2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
Caenorhabditis elegans
2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
Corynebacterium diphtheriae
2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
Klebsiella pneumoniae
2-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-3-(4-iodophenyl)propanoic acid
-
Mycobacterium tuberculosis
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
3-(3-(2-(allylamino)thiazol-4-yl)-2,5-dimethyl-1H-pyrrol-1-yl)propanoic acid
-
Klebsiella pneumoniae
3-(3-(2-(allylamino)thiazol-4-yl)-2,5-dimethyl-1H-pyrrol-1-yl)propanoic acid
-
Mycobacterium tuberculosis
3-(6-(benzyloxy)-1H-indol-1-yl)propanoic acid
-
Klebsiella pneumoniae
3-(6-(benzyloxy)-1H-indol-1-yl)propanoic acid
-
Mycobacterium tuberculosis
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
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
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
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)

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

Organism

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

Substrates and Products (Substrate)

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

Synonyms

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

Cofactor

Cofactor Comment Organism Structure
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
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
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
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

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