Title: Rate-Dependent Inverse-Addition beta-Selective Mannosylation and Contiguous Sequential Glycosylation Involving beta-Mannosidic Bond Formation
Authors: Chang, Shih-Sheng
Shih, Che-Hao
Lai, Kwun-Cheng
Mong, Kwok-Kong Tony
Department of Applied Chemistry
Keywords: glycosylation;inverse addition;mannosylation;oligosaccharides;beta-selectivity
Issue Date: 2010
Abstract: "The beta-selectivity of mannosylation has been found to be dependent on the addition rate of the mannosyl trichloroacetimidate donor in an inverse-addition (I-A) procedure. This rate dependent I-A procedure can improve the selectivity of direct beta-mannosylation and is applicable to orthogonal glycosylations of thioglycoside acceptors. Further elaboration of this novel procedure enables the development of the contiguous sequential glycosylation strategy, which streamlines the preparation of oligosaccharides invoking beta-mannosidic bond formation. The synthetic utility of the contiguous glycosylation strategy was demonstrated by the preparation of the trisaccharide core of human N-linked glycoproteins and the trisaccharide repeating unit of the O-specific polysaccharide found in the cellular capsule of Salmonelle bacteria."
URI: http://hdl.handle.net/11536/16684
ISSN: 1861-4728
Volume: 5
Issue: 5
End Page: 1152
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