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Literature summary for 3.2.1.180 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

Inhibitors Comment Organism Structure
(2R)-pyrrolidinium-2-carboxylate
-
Clostridium perfringens
(2R,3R,4S,5S,6R)-3,4,5,6-tetrahydroxypiperidine-2-carboxylic acid competitive Clostridium perfringens
(2S)-pyrrolidinium-2-carboxylate
-
Clostridium perfringens
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid competitive Clostridium perfringens
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]

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

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
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

Organism UniProt Comment Textmining
Clostridium perfringens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,4,6-trichlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
2,4-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
2,5-dinitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-4-O-sulfo-D-galactopyranose + H2O
-
Clostridium perfringens ?
-
?
2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-6-O-sulfo-D-galactopyranose + H2O
-
Clostridium perfringens ?
-
?
2-(acetylamino)-2-deoxy-3-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-D-galactopyranose + H2O
-
Clostridium perfringens ?
-
?
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
-
?
2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl)-2-(sulfoamino)-D-glucopyranose + H2O
-
Clostridium perfringens ?
-
?
3-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
4-chlorophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
4-deoxy-alpha-L-threo-hex-4-enopyranuronosyl fluoride + H2O an unsaturated glucuronyl fluoride giving very low activity Clostridium perfringens ?
-
?
4-deoxy-beta-L-threo-hex-4-enopyranuronosyl fluoride + H2O an unsaturated glucuronyl fluoride giving very low activity Clostridium perfringens ?
-
?
4-nitrophenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
4-tert-butylphenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
benzyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?
additional information unsaturated glucuronyl hydrolases acts on the unsaturated uronic-acid-containing oligosaccharides to remove the unusual non-reducing terminal monomer units Clostridium perfringens ?
-
?
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 ?
-
?
phenyl 4-deoxy-alpha-L-threo-hex-4-enopyranosiduronic acid + H2O
-
Clostridium perfringens ?
-
?

Synonyms

Synonyms Comment Organism
UGL
-
Clostridium perfringens
unsaturated glucuronyl hydrolase
-
Clostridium perfringens

Temperature Optimum [°C]

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

Turnover Number [1/s]

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

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

IC50 Value

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

General Information

General Information Comment Organism
metabolism the enzyme is involved in the metabolic pathway for degradation of glycosaminoglycans Clostridium perfringens
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
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]

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