Synthesis of a deuterated analogue of bacteriohopanetetrol-glucosamine, a probe of complex hopanoid biosynthesis.
This study reports the straightforward preparation of a deuterated biohopanoid that will be used to probe a new biosynthetic pathway. This multistep hemisynthesis required a stereoselective glycosylation, a regioselective deuteration as well as a properly defined strategy for the final deprotections and the purification of the amphiphilic final glycoside.
Pan
Weidong
W
University of Namur (FUNDP), Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000, Namur, Belgium.
Vincent
Stéphane P
SP
D003903:Deuterium / Q000737:chemistry*; D005944:Glucosamine / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D013237:Stereoisomerism; D013379:Substrate Specificity; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*
D006027:Glycosides; D014315:Triterpenes; C054760:32,33,34,35-bacteriohopanetetrol; D003903:Deuterium; D005944:Glucosamine