Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation–Desulfurization Chemistry
Field | Value | Language |
dc.contributor.author | Sayers, Jessica | |
dc.contributor.author | Thompson, Robert E. | |
dc.contributor.author | Perry, Kristen J. | |
dc.contributor.author | Malins, Lara R. | |
dc.contributor.author | Payne, Richard J. | |
dc.date.accessioned | 2020-05-11 | |
dc.date.available | 2020-05-11 | |
dc.date.issued | 2015-09-23 | |
dc.identifier.uri | https://pubs.acs.org/doi/10.1021/acs.orglett.5b02468 | |
dc.identifier.uri | https://hdl.handle.net/2123/22250 | |
dc.description.abstract | The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the β-thiol asparagine moiety for rapid ligation reactions with peptide thioesters. The streamlined synthesis of native peptide products could be accomplished using a one-pot radical desulfurization of the β-thiol auxiliary following the ligation event. The utility of the amino acid is highlighted in the efficient one-pot assembly of the HIV entry inhibitor enfuvirtide. | en_AU |
dc.language.iso | en_US | en_AU |
dc.publisher | American Chemical Society | en_AU |
dc.relation | ARC FT130100150 | en_AU |
dc.rights | Copyright © 2015 American Chemical Society | |
dc.subject | High-performance liquid chromatography | en_AU |
dc.subject | Peptides and proteins | en_AU |
dc.subject | Monomers | en_AU |
dc.subject | Ligation | en_AU |
dc.subject | Desulfurization | en_AU |
dc.title | Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation–Desulfurization Chemistry | en_AU |
dc.type | Article | en_AU |
dc.subject.asrc | FoR::030599 - Organic Chemistry not elsewhere classified | en_AU |
dc.subject.asrc | FoR::030499 - Medicinal and Biomolecular Chemistry not elsewhere classified | en_AU |
dc.identifier.doi | 10.1021/acs.orglett.5b02468 | |
dc.type.pubtype | Post-print | en_AU |
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