Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
10596030 | Bioorganic & Medicinal Chemistry Letters | 2013 | 5 Pages |
Abstract
A series of novel glycopyranosyl azides were synthesised wherein the carbohydrate moiety was peracylated with four acetyl, propionyl, butanoyl, pentanoyl (valeryl) or 3-methylbutanoyl (isovaleryl) ester linked groups. A panel of glycoconjugates was synthesised from these glycopyranosyl azides using copper-catalysed azide-alkyne cycloaddition. The in vitro metabolic stability, plasma stability and plasma protein binding was then measured to establish the impact of the different acyl group when presented on a common scaffold. The acetyl, propionyl and butanoyl esters exhibited metabolism consistent with esterase processing, and various mono-, di- and tri-acylated hydrolysis products as well as the fully hydrolysed compound were detected. In contrast, the pentanoyl and 3-methylbutanoyl esters were stable.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Cindy J. Carroux, Janina Moeker, Josephine Motte, Marie Lopez, Laurent F. Bornaghi, Kasiram Katneni, Eileen Ryan, Julia Morizzi, David M. Shackleford, Susan A. Charman, Sally-Ann Poulsen,