A serendipitous formation of a cysteine-bridged disaccharide

Nokwequ, M G; Nkambule, C M; Gammon, D W

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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
dc.identifier.apacitation	Nokwequ, 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/11427/19701	en_ZA
dc.identifier.chicagocitation	Nokwequ, 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/11427/19701	en_ZA
dc.identifier.vancouvercitation	Nokwequ 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.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