A serendipitous formation of a cysteine-bridged disaccharide

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dc.contributor.authorNokwequ, M G
dc.contributor.authorNkambule, C M
dc.contributor.authorGammon, D W
dc.date.accessioned2016-05-17T12:18:28Z
dc.date.available2016-05-17T12:18:28Z
dc.date.issued2014
dc.date.updated2016-05-17T12:15:11Z
dc.description.abstractN-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.identifier.apacitationNokwequ, M. G., Nkambule, C. M., & Gammon, D. W. (2014). A serendipitous formation of a cysteine-bridged disaccharide. <i>South African Journal of Chemistry-Suid-Afrikaanse Tydskrif Vir Chemie</i>, http://hdl.handle.net/11427/19701en_ZA
dc.identifier.chicagocitationNokwequ, M G, C M Nkambule, and D W Gammon "A serendipitous formation of a cysteine-bridged disaccharide." <i>South African Journal of Chemistry-Suid-Afrikaanse Tydskrif Vir Chemie</i> (2014) http://hdl.handle.net/11427/19701en_ZA
dc.identifier.citationNokwequ, 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.issn0379-4350en_ZA
dc.identifier.ris TY - Journal Article AU - Nokwequ, M G AU - Nkambule, C M AU - Gammon, D W AB - 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. DA - 2014 DB - OpenUCT DP - University of Cape Town J1 - South African Journal of Chemistry-Suid-Afrikaanse Tydskrif Vir Chemie LK - https://open.uct.ac.za PB - University of Cape Town PY - 2014 SM - 0379-4350 T1 - A serendipitous formation of a cysteine-bridged disaccharide TI - A serendipitous formation of a cysteine-bridged disaccharide UR - http://hdl.handle.net/11427/19701 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/19701
dc.identifier.vancouvercitationNokwequ MG, Nkambule CM, Gammon DW. A serendipitous formation of a cysteine-bridged disaccharide. South African Journal of Chemistry-Suid-Afrikaanse Tydskrif Vir Chemie. 2014; http://hdl.handle.net/11427/19701.en_ZA
dc.languageengen_ZA
dc.languageafren_ZA
dc.languagexhoen_ZA
dc.publisherSouth African Chemical Instituteen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.rightsCreative Commons Attribution 4.0 International (CC BY 4.0)*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en_ZA
dc.sourceSouth African Journal of Chemistry-Suid-Afrikaanse Tydskrif Vir Chemieen_ZA
dc.source.urihttp://www.journals.co.za/sajchem/
dc.subject.otherglycopeptides
dc.subject.otherglycosylation
dc.subject.otherbridged-disaccharides
dc.titleA serendipitous formation of a cysteine-bridged disaccharideen_ZA
dc.typeJournal Articleen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceArticleen_ZA
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