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MetaCyc Compound Class: chondroitin sulfate A

Synonyms: chondroitin 4-sulfate

Superclasses: all carbohydrates a carbohydrate a glycan a polysaccharide a glycosaminoglycan chondroitin sulfate

Summary:
Chondroitin sulfate is a sulfated glycosaminoglycan composed of alternating units of N-acetyl-β-D-galactosamine and β-D-glucuronate. It is usually found attached to proteins as part of a proteoglycan.

The saccharide units can be sulfated in variable positions and quantities - N-acetyl-β-D-galactosamine can be sulfated at positions 4 and 6 to yield N-acetyl-β-D-galactosamine 4-sulfate, N-acetyl-β-D-galactosamine 6-O-sulfate or N-acetyl-D-galactosamine 4,6-bissulfate, while β-D-glucuronate can be sulfated at position 2 to form 2-O-sulfo-β-D-glucuronate.

The following names have been used to define different sulfation states:

Chondroitin sulfate A contains β-D-glucuronate and N-acetyl-β-D-galactosamine 4-sulfate

Chondroitin sulfate C contains β-D-glucuronate and N-acetyl-β-D-galactosamine 6-O-sulfate

Chondroitin sulfate D contains 2-O-sulfo-β-D-glucuronate and N-acetyl-β-D-galactosamine 6-O-sulfate

Chondroitin sulfate E contains β-D-glucuronate and N-acetyl-D-galactosamine 4,6-bissulfate

The term "chondroitin sulfate B" has been used in the past to refer to dermatan sulfate, but is not used any more.

SMILES: CC(=O)NC2(C(O[R1])OC(CO)C(OS(=O)(=O)[O-])C(OC1(OC(C(O)=O)C(O[R2])C(O)C(O)1))2)

Reactions known to consume the compound:

chondroitin sulfate and dermatan sulfate degradation I (bacterial) :
chondroitin sulfate A(n)chondroitin sulfate A(n-1) + 4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine 4-sulfate
chondroitin sulfate A → n 4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine 4-sulfate
chondroitin sulfate A → n 4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine 4-sulfate

chondroitin sulfate degradation (metazoa) :
chondroitin sulfateN-acetyl-β-D-galactosamine + β-D-glucuronate

Not in pathways:
chondroitin sulfate + n H2O → n chondroitin sulfate disaccharide


a polysaccharide + H2O → an oligosaccharide

Reactions known to produce the compound:

cellulose and hemicellulose degradation (cellulolosome) :
a feruloyl-polysaccharide + H2O → ferulate + a polysaccharide + 2 H+

Not in pathways:
an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

In Reactions of unknown directionality:

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

Enzymes inhibited by chondroitin sulfate A, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: keratan galactose-6-sulfatase [Glossl79] , chondroitin N-acetylgalactosamine-6-sulfatase [Glossl79]

Credits:
Created 28-Jul-2010 by Caspi R , SRI International


References

Glossl79: Glossl J, Truppe W, Kresse H (1979). "Purification and properties of N-acetylgalactosamine 6-sulphate sulphatase from human placenta." Biochem J 181(1);37-46. PMID: 39554

Trowbridge02: Trowbridge JM, Gallo RL (2002). "Dermatan sulfate: new functions from an old glycosaminoglycan." Glycobiology 12(9);117R-25R. PMID: 12213784


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 18.5 on Sat Nov 22, 2014, biocyc14.