Synthesis of Sulfoquinovose and Sulfoquinovosyl Diacylglycerides, and a Fluorogenic Substrate for Sulfoquinovosidases

02 December 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


sulfur cycle
organic chemistry

Supplementary materials

SI 261119


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