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

preprint
submitted on 26.11.2019 and posted on 02.12.2019 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.

Funding

Using chemistry to illuminate sulfoglycolysis, a major organosulfur pathway

Australian Research Council

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Australian Synchrotron (proposal 13618b)

History

Email Address of Submitting Author

sjwill@unimelb.edu.au

Institution

University of Melbourne

Country

Australia

ORCID For Submitting Author

0000-0001-6341-4364

Declaration of Conflict of Interest

no conflict of interest

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