"Sweet silicones": biocatalytic reactions to form organosilicon carbohydrate macromers.

Org Lett

NSF IUCRC for Biocatalysis and Bioprocessing of Macromolecules, Othmer Department of Chemical and Biological Sciences and Engineering, Polytechnic University, Six Metrotech Center, Brooklyn, NY 11201, USA.

Published: September 2005

Immobilized lipase B from Candida antarctica (Novozyme 435) catalyzed the regioselective formation of ester bonds between organosilicon carboxylic diacids and a C1-O-alkylated sugar under mild reaction conditions (i.e., low temperature, neutral pH, solventless). Specifically, the acid-functionalized organosilicones reacted with the primary hydroxyl group at the C6 position of alpha,beta-ethyl glucoside during the regioselective esterification. The pure organosilicon-sugar conjugates were prepared in a one-step reaction without protection-deprotection steps and without activation of the acid groups with the integrity of the siloxane bonds. [reaction: see text]

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http://dx.doi.org/10.1021/ol050942eDOI Listing

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