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

submitted on 26.11.2019, 11:43 and posted on 02.12.2019, 09:12 by Yunyang Zhang, Janice Mui, Thimali Arumaperuma, James P. Lingford, ETHAN GODDARD-BORGER, JONATHAN WHITE, Spencer Williams

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.


Using chemistry to illuminate sulfoglycolysis, a major organosulfur pathway

Australian Research Council

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Australian Synchrotron (proposal 13618b)


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University of Melbourne



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no conflict of interest