A serendipitous formation of a cysteine-bridged disaccharide

 

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dc.contributor.author Nokwequ, M G
dc.contributor.author Nkambule, C M
dc.contributor.author Gammon, D W
dc.date.accessioned 2016-05-17T12:18:28Z
dc.date.available 2016-05-17T12:18:28Z
dc.date.issued 2014
dc.identifier.citation Nokwequ, M. G., Nkambule, C. M., & Gammon, D. W. (2014). A serendipitous formation of a cysteine-bridged disaccharide. South African Journal of Chemistry, 67, 180-183. en_ZA
dc.identifier.issn 0379-4350 en_ZA
dc.identifier.uri http://hdl.handle.net/11427/19701
dc.description.abstract N-acetyl-L-cysteine bearing free carboxylic acid and sulfhydryl groups was glycosylated with 1,2,3,4,6-Penta-O-acetyl-ß-D-glucopyranoside in the presence of SnCl4 as a promoter to give the S-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 pKa 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. en_ZA
dc.language eng en_ZA
dc.language afr en_ZA
dc.language xho en_ZA
dc.publisher South African Chemical Institute en_ZA
dc.rights Creative Commons Attribution 4.0 International (CC BY 4.0) *
dc.rights.uri http://creativecommons.org/licenses/by/4.0/ en_ZA
dc.source South African Journal of Chemistry-Suid-Afrikaanse Tydskrif Vir Chemie en_ZA
dc.source.uri http://www.journals.co.za/sajchem/
dc.subject.other glycopeptides
dc.subject.other glycosylation
dc.subject.other bridged-disaccharides
dc.title A serendipitous formation of a cysteine-bridged disaccharide en_ZA
dc.type Journal Article en_ZA
dc.date.updated 2016-05-17T12:15:11Z
uct.type.publication Research en_ZA
uct.type.resource Article en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
uct.type.filetype Text
uct.type.filetype Image


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Creative Commons Attribution 4.0 International (CC BY 4.0) Except where otherwise noted, this item's license is described as Creative Commons Attribution 4.0 International (CC BY 4.0)