dc.contributor.author |
Ahangarpour, Marzieh |
|
dc.contributor.author |
Kavianinia, Iman |
|
dc.contributor.author |
Hume, Paul A |
|
dc.contributor.author |
Harris, Paul WR |
|
dc.contributor.author |
Brimble, Margaret A |
|
dc.coverage.spatial |
United States |
|
dc.date.accessioned |
2023-05-23T04:34:47Z |
|
dc.date.available |
2023-05-23T04:34:47Z |
|
dc.date.issued |
2022-08 |
|
dc.identifier.citation |
(2022). Journal of the American Chemical Society, 144(30), 13652-13662. |
|
dc.identifier.issn |
0002-7863 |
|
dc.identifier.uri |
https://hdl.handle.net/2292/64127 |
|
dc.description.abstract |
Herein we report the first examples of thiol-selective heterobifunctional electrophiles, <i>N</i>-vinyl acrylamides, that enable efficient highly selective thiol-thiol bioconjugations and cysteine modification of peptides. We demonstrate that these new classes of thiol-selective scaffolds can readily undergo a thia-Michael addition and an orthogonal radical induced thiol-ene "click" reaction under biocompatible conditions. Furthermore, the formation of an unexpected Markovnikov <i>N</i>,<i>S</i>-acetal hydrothiolation was explained using computational studies. We also reveal that <i>N</i>-methylation of the <i>N</i>-vinyl acrylamide scaffold changes the regioselectivity of the reaction. We demonstrate that use of <i>N</i>-vinyl acrylamides shows promise as an efficient, mild, and exquisite cysteine-selective protocol for facile construction of fluorophore-labeled peptides and proteins and that the resultant conjugates are resistant to degradation and thiol exchange, thus significantly improving their biophysical properties. |
|
dc.format.medium |
Print-Electronic |
|
dc.language |
eng |
|
dc.publisher |
American Chemical Society (ACS) |
|
dc.relation.ispartofseries |
Journal of the American Chemical Society |
|
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. |
|
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
|
dc.subject |
Acrylamides |
|
dc.subject |
Sulfhydryl Compounds |
|
dc.subject |
Cysteine |
|
dc.subject |
Peptides |
|
dc.subject |
Proteins |
|
dc.subject |
03 Chemical Sciences |
|
dc.title |
<i>N</i>-Vinyl Acrylamides: Versatile Heterobifunctional Electrophiles for Thiol-Thiol Bioconjugations. |
|
dc.type |
Journal Article |
|
dc.identifier.doi |
10.1021/jacs.2c04146 |
|
pubs.issue |
30 |
|
pubs.begin-page |
13652 |
|
pubs.volume |
144 |
|
dc.date.updated |
2023-04-29T06:58:10Z |
|
dc.rights.holder |
Copyright: The authors |
en |
dc.identifier.pmid |
35858283 (pubmed) |
|
pubs.author-url |
https://www.ncbi.nlm.nih.gov/pubmed/35858283 |
|
pubs.end-page |
13662 |
|
pubs.publication-status |
Published |
|
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RetrictedAccess |
en |
pubs.subtype |
Journal Article |
|
pubs.elements-id |
913179 |
|
pubs.org-id |
Science |
|
pubs.org-id |
Chemistry |
|
pubs.org-id |
Biological Sciences |
|
pubs.org-id |
Science Research |
|
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
|
dc.identifier.eissn |
1520-5126 |
|
pubs.record-created-at-source-date |
2023-04-29 |
|
pubs.online-publication-date |
2022-07-20 |
|