The structure of chondroitin sulfate shown in the article
is ambiguous in at least two instances. 1) The oxygen linkages on the
far right and between rings are actually glycosidic, that is, the oxygens
are part of acetal functional groups, and not bonded to a -CH2- as denoted
by the "bend" in the line connecting the ring to the oxygen.
2) The stereochemistry at C-4 on the left-hand ring is not specified. The left ring is is from D-glucuronic acid which is derived
from D-glucose. Knowing this, you can draw a Fisher projection of D-glucuronic
acid. How might the carboxylate substituent have been formed
from glucose? The right ring is said to be from N-acetylglucosamine
sulfate. Most names of this sort imply an amine salt (R4N+X-), but here
the sulfate is a covalently bonded substituent group. Explain why the
N-acetyl (amide) group is not basic. Very probably, the right ring residue is either named
incorrectly or drawn incorrectly. If drawn correctly, the residue is N-acetylgalactosamine-4-sulfate.
Explain why this might be a better name for the residue (hint: draw the
Fisher, then Haworth, structures of glucose and galactose). Specify the type of glycosidic residue between the two sugar residues (e.g. alpha/beta(n --> n')).
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