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MetaCyc Compound Class: [chondroitin]-β-D-glucuronate

Synonyms: [dermatan]-β-D-glucuronate

Superclasses: all carbohydrates a carbohydrate a glycan a glycosaminoglycan a galactosaminoglycan chondroitin-[core protein]
an acid all carboxy acids a carboxylate

Summary:
Chondroitin sulfate is a glycosaminoglycan found mostly attached to proteins as part of a proteoglycan. Chondroitin sulfate is composed of repeating disaccharide units composed of a hexuronic acid and a hexose sugar, specifically β-D-glucuronate and N-acetyl-β-D-galactosamine linked by β(1 -> 3) linkages. Both units are often sulfated.

This compound stand for β-D-glucuronate (not-sulfated) within the context of chondroitin sulfate.

[chondroitin]-β-D-glucuronate compound structure

SMILES: C1(O[R2])(C(O)C(C(O[R1])C(C(=O)[O-])O1)O)

Reactions known to consume the compound:

chondroitin sulfate biosynthesis (late stages) :
[chondroitin]-β-D-glucuronate + 3'-phosphoadenylyl-sulfate → [chondroitin-sulfate]-2-O-sulfo-β-D-glucuronate + adenosine 3',5'-bisphosphate + H+

dermatan sulfate biosynthesis (late stages) :
[chondroitin]-β-D-glucuronate → [dermatan]-α-L-iduronate

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

Not in pathways:
[chondroitin-sulfate]-2-O-sulfo-β-D-glucuronate + H2O → [chondroitin]-β-D-glucuronate + sulfate + H+

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a β-monogalactosyldiacylglycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

chondroitin biosynthesis , chondroitin sulfate biosynthesis (late stages) :
N-acetyl-D-galactosaminyl-(1→4)-β-D-glucuronyl-(1→3)-β-N-acetyl-D-galactosaminyl-(1→4)-β-D-glucuronyl-(1→3)-β-D-galactosyl-(1->3)-β-D-galactosyl-(1->4)-β-D-xylosyl-[core protein] = chondroitin-[core protein]

Not in pathways:
UDP-α-D-galactose + a glycosaminoglycan = a D-galactosylglycosaminoglycan + UDP + H+

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

Credits:
Created 29-Jul-2010 by Caspi R , SRI International


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Thu Jul 2, 2015, BIOCYC13A.