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oa South African Journal of Chemistry - A serendipitous formation of a cysteine-bridged disaccharide : research article

 

Abstract

-acetyl-L-cysteine bearing free carboxylic acid and sulfhydryl groups was glycosylated with 1,2,3,4,6-Penta--acetyl-β-D-glucopyranoside in the presence of SnCl as a promoter to give the -glycosylated cysteine in 64% yield. However, when excess donor was used, a previously unreported cysteine-bridged disaccharide was isolated in 54% yield. The acetamido group on cysteine, which lowers the p of the carboxylic acid group of the amino acid, plays no role in the formation of the bridged disaccharide since 3-mercaptopropionic acid reacts in a similar manner to give the 3-mercaptopropionic acid-bridged disaccharide in 52% yield.

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/content/chem/67/1/EJC161063
2014-01-01
2016-12-04
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