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Literature summary for 4.2.2.5 extracted from
- Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum (2002), J. Am. Chem. Soc., 124, 9756-9767.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| benzyl 4-deoxy-5-fluoro-beta-D-galactopyranosiduronic acid | competitive inhibition | Pedobacter heparinus |  |
| phenyl 4-deoxy-4,4-difluoro-beta-D-xylo-hexopyranosiduronic acid | competitive inhibition | Pedobacter heparinus | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | kinetics, measurement of deuterium isotope effects | Pedobacter heparinus | |
| 1 | - |
phenyl 4-methylumbelliferyl-beta-D-glucopyranosiduronic acid | pH 8.0 | Pedobacter heparinus | |
| 7 | - |
benzyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 9 | - |
benzyl 4-O-(3',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 12.2 | - |
benzyl 4-O-(4'-chloro-2'-nitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 16.9 | - |
benzyl 4-O-(2'-nitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 28 | - |
benzyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | - |
Pedobacter heparinus | |
| 114 | - |
phenyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | - |
Pedobacter heparinus | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Pedobacter heparinus | - |
- |
- |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine] | acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate, stepwise reaction mechanism | Pedobacter heparinus |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| benzyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| benzyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| benzyl 4-O-(2'-nitrophenyl)-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| benzyl 4-O-(3',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| benzyl 4-O-(4'-chloro-2'-nitrophenyl)-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| chondroitin sulfate A | i.e. chondroitin 4-sulfate | Pedobacter heparinus | ? | - |
? | |
| chondroitin sulfate C | i.e. chondroitin 6-sulfate | Pedobacter heparinus | ? | - |
? | |
| methyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| additional information | elimination mechanism, but no syn-elimination, resulting in disaccharides or oligosaccharides with DELTA4,5-unsaturated uronic acid residues at the nonreducing end | Pedobacter heparinus | ? | - |
? | |
| phenyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
| phenyl 4-methylumbelliferyl-beta-D-glucopyranosiduronic acid | synthetic chromogenic substrate | Pedobacter heparinus | ? | - |
? | |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0016 | - |
phenyl 4-methylumbelliferyl-beta-D-glucopyranosiduronic acid | pH 8.0 | Pedobacter heparinus | |
| 0.019 | - |
benzyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 0.019 | - |
benzyl 4-O-(3',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 0.027 | - |
benzyl 4-O-(2'-nitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 0.035 | - |
benzyl 4-O-(4'-chloro-2'-nitrophenyl)-beta-D-glucopyranosiduronic acid | pH 6.8 | Pedobacter heparinus | |
| 0.16 | - |
benzyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | - |
Pedobacter heparinus | |
| 2.3 | - |
phenyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid | - |
Pedobacter heparinus | |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 3 | - |
benzyl 4-deoxy-5-fluoro-beta-D-galactopyranosiduronic acid | - |
Pedobacter heparinus | |
| 24 | - |
phenyl 4-deoxy-4,4-difluoro-beta-D-xylo-hexopyranosiduronic acid | - |
Pedobacter heparinus | |
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