Concise synthesis of sulfoquinovose and sulfoquinovosyl diacylglycerides, and development of a fluorogenic substrate for sulfoquinovosidases
- Author(s)
- Zhang, Y; Mui, JW; Arumaperuma, T; Lingford, JP; Goddard-Borger, ED; White, JM; Williams, SJ;
- Journal Title
- Organic & Biomolecular Chemistry
- Publication Type
- Journal Article in press
- Abstract
- 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 alpha-d-sulfoquinovoside, and examination of its cleavage kinetics by two recombinant SQases. These compounds will assist in dissecting the role of sulfoglycolysis in the biogeochemical sulfur cycle and understanding the molecular basis of sulfoglycolysis.
- Publisher
- Royal Society of Chemistry
- Research Division(s)
- Chemical Biology
- PubMed ID
- 31894821
- Publisher's Version
- https://doi.org/10.1039/c9ob02540e
- NHMRC Grants
- NHMRC/1100164, NHMRC/1139549,
- ARC Grants
- ARC/DP180101957,
- Terms of Use/Rights Notice
- Refer to copyright notice on published article.
Creation Date: 2020-02-24 09:56:02
Last Modified: 2020-02-24 12:39:47