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Concise synthesis of sulfoquinovose and sulfoquinovosyl diacylglycerides, and development of a fluorogenic substrate for sulfoquinovosidases.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-01-02 , DOI: 10.1039/c9ob02540e
Yunyang Zhang 1 , Janice W-Y Mui 1 , Thimali Arumaperuma 1 , James P Lingford 2 , Ethan D Goddard-Borger 2 , Jonathan M White 1 , Spencer J Williams 1
Affiliation  

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 compounds will assist in dissecting the role of sulfoglycolysis in the biogeochemical sulfur cycle and understanding the molecular basis of sulfoglycolysis.

中文翻译:

磺基喹诺酮糖和磺基喹喔基二酰基甘油酯的简明合成,以及磺基喹喔啉酶的荧光底物的开发。

据估计,硫脂基磺基喹喔基二酰基甘油(SQDG)及其首基磺基糖磺基基诺糖(SQ)占据了生物圈中所有有机硫的一半。SQ通过磺基喹喔啉酶(SQases)的作用从SQDG和相关的糖苷中释放出来。我们报告了SQDG的10个步骤的合成,我们将其用于制备饱和和不饱和脂质形式。我们还报告了SQ和(13C6)SQ的快速合成,以及SQ的钠盐和钾盐的X射线晶体结构。最后,我们报告了荧光SQase底物,甲基伞形酮α-d-磺基喹诺酮苷的合成,并通过两个重组SQases对其裂解动力学进行了检查。这些化合物将有助于剖析磺基糖解作用在生物地球化学硫循环中的作用,并有助于理解磺基糖解作用的分子基础。
更新日期:2020-02-10
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