Synthesis of Sulfoquinovose and Sulfoquinovosyl Diacylglycerides, and a Fluorogenic Substrate for Sulfoquinovosidases
semanticscholar(2019)
摘要
The
sulfolipid sulfoquinovosyl diacylglycerol (SQDG) and its headgroup, the
sulfosugar sulfoquinovose (SQ), are estimated to harbour up to half of all
organosulfur in the biosphere. SQ is liberated from SQDG and related glycosides
by the action of sulfoquinovosidases (SQases). We report a 10-step synthesis of
SQDG that we apply to the preparation of saturated and unsaturated lipoforms. We
also report an expeditious synthesis of SQ and (13C6)SQ,
and X-ray crystal structures of sodium and potassium salts of SQ. Finally, we
report the synthesis of a fluorogenic SQase substrate, methylumbelliferyl a-D-sulfoquinovoside, and examination
of its cleavage kinetics by two recombinant SQases.
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