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Literature summary extracted from

  • Jongkees, S.A.; Yoo, H.; Withers, S.G.
    Mechanistic insights from substrate preference in unsaturated glucuronyl hydrolase (2014), ChemBioChem, 15, 124-134.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.180 (2R)-pyrrolidinium-2-carboxylate
-
 Clostridium perfringens
3.2.1.180 (2R,3R,4S,5S,6R)-3,4,5,6-tetrahydroxypiperidine-2-carboxylic acid competitive Clostridium perfringens
3.2.1.180 (2S)-pyrrolidinium-2-carboxylate
-
 Clostridium perfringens
3.2.1.180 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid competitive Clostridium perfringens
3.2.1.180 additional information several analogues designed to take advantage ofstrong enzyme binding to the reaction's transition state show little to no inhibition. No inhibition by 17a and 17b Clostridium perfringens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.1.180 additional information
-
 additional information Michaelis-Menten kinetic parameters for the cleavage of a variety of unsaturated disaccharides of glycosaminoglycan origin, overview Clostridium perfringens
3.2.1.180 0.16
-
 2,4-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.26
-
 4-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.58
-
 2,4,6-trichlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.59
-
 2,5-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.84
-
 4-chlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.88
-
 3-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.88
-
 4-tert-butylphenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 1.2
-
 2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-2-(sulfoamino)-D-glucopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 3
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 3.2
-
 phenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 3.7
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 4.5
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-4-O-sulfo-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 9
-
 benzyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.180 additional information Clostridium perfringens unsaturated glucuronyl hydrolases acts on the unsaturated uronic-acid-containing oligosaccharides to remove the unusual non-reducing terminal monomer units ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.180 Clostridium perfringens
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.180 2,4,6-trichlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 2,4-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 2,5-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-4-O-sulfo-D-galactopyranose + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-galactopyranose + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-D-galactopyranose + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 2-acetamido-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-galactopyranose + H2O high activity, a substrate with sulfation of the primary alcohol on carbon 6 of its N-acetylgalactosamine moiety Clostridium perfringens 2-acetamido-2-deoxy-6-O-sulfo-D-galactopyranose + 4-deoxy-alpha-L-threo-hex-4-enopyranose
-
 ?
3.2.1.180 2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-2-(sulfoamino)-D-glucopyranose + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 3-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 4-chlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl fluoride + H2O an unsaturated glucuronyl fluoride giving very low activity Clostridium perfringens ?
-
 ?
3.2.1.180 4-deoxy-beta-L-threo-hex-4-enopyranuronosyl fluoride + H2O an unsaturated glucuronyl fluoride giving very low activity Clostridium perfringens ?
-
 ?
3.2.1.180 4-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 4-tert-butylphenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 benzyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?
3.2.1.180 additional information unsaturated glucuronyl hydrolases acts on the unsaturated uronic-acid-containing oligosaccharides to remove the unusual non-reducing terminal monomer units Clostridium perfringens ?
-
 ?
3.2.1.180 additional information no or poor activity with 2-(acetylamino)-2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-glucopyranose and 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-2-O-sulfo-alpha-L-threo-hex-4-enopyranuronosyl)-D-galactopyranose Clostridium perfringens ?
-
 ?
3.2.1.180 phenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
 Clostridium perfringens ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.1.180 UGL
-
 Clostridium perfringens
3.2.1.180 unsaturated glucuronyl hydrolase
-
 Clostridium perfringens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.1.180 37
-
 assay at Clostridium perfringens

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.2.1.180 0.09
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-4-O-sulfo-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.14
-
 2,4-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.312
-
 2,4,6-trichlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.64
-
 2,5-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 2.05
-
 4-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 3.27
-
 4-tert-butylphenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 3.9
-
 4-chlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 4.3
-
 phenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 8.5
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 14
-
 2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-2-(sulfoamino)-D-glucopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 14.7
-
 3-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 18.6
-
 benzyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 112
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-galactopyranose pH 6.6, 37°C Clostridium perfringens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.2.1.180 6.6
-
 assay at Clostridium perfringens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.2.1.180 3
-
 pH 6.6, 37°C Clostridium perfringens (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
3.2.1.180 7.2
-
 pH 6.6, 37°C Clostridium perfringens (2R,3R,4S,5S,6R)-3,4,5,6-tetrahydroxypiperidine-2-carboxylic acid

General Information

EC Number General Information Comment Organism
3.2.1.180 metabolism the enzyme is involved in the metabolic pathway for degradation of glycosaminoglycans Clostridium perfringens
3.2.1.180 additional information a hydration-initiated mechanism with a transition state with positive charge at carbon 5 and the endocyclic oxygen is proposed, transition-state structure for the first irreversible step of this mechanism, overview Clostridium perfringens
3.2.1.180 physiological function unsaturated glucuronyl hydrolases acts on the unsaturated uronic-acid-containing oligosaccharides to remove the unusual non-reducing terminal monomer units Clostridium perfringens

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.2.1.180 0.000044
-
 4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl fluoride pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.02
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-4-O-sulfo-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.55
-
 2,4,6-trichlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 0.9
-
 2,4-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 1.1
-
 2,5-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 1.3
-
 phenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 2.1
-
 benzyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 2.8
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-D-galactopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 3.7
-
 4-tert-butylphenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 4.6
-
 4-chlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 7.9
-
 4-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 12
-
 2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-2-(sulfoamino)-D-glucopyranose pH 6.6, 37°C Clostridium perfringens
3.2.1.180 16
-
 3-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid pH 6.6, 37°C Clostridium perfringens
3.2.1.180 30
-
 2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-galactopyranose pH 6.6, 37°C Clostridium perfringens