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
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|
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/
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|
dc.subject.other |
glycopeptides |
|
dc.subject.other |
glycosylation |
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dc.subject.other |
bridged-disaccharides |
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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 -
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en_ZA |