Concise synthesis of sulfoquinovose and sulfoquinovosyl diacylglycerides, and development of a fluorogenic substrate for sulfoquinovosidases
Yunyang Zhang, Janice W-Y Mui, Thimali Arumaperuma, James P Lingford, Ethan D Goddard-Borger, Jonathan M White, Spencer J Williams
ORGANIC & BIOMOLECULAR CHEMISTRY | ROYAL SOC CHEMISTRY | Published : 2020
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 α-d-sulfoquinovoside, and examination of its cleavage kinetics by two recombinant SQases. These com..View full abstract
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Awarded by Australian Research Council
Awarded by National Health and Medical Research Council of Australia
This work was supported by grants from the Australian Research Council (DP180101957) and the National Health and Medical Research Council of Australia (APP1100164, GNT1139549); support from The Walter and Eliza Hall Institute of Medical Research, the Australian Cancer Research Fund, and a Victorian State Government Operational Infrastructure support grant. We gratefully acknowledge the Australian Synchrotron for beamtime via the Collaborative Access Program (proposal number 13618b). J. W.-Y. M. is supported by a Sir John and Lady Higgins Research Scholarship.