Journal
ORGANIC LETTERS
Volume 17, Issue 19, Pages 4902-4905Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02468
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Funding
- Australian Research Council (ARC) [FT130100150]
- Northcote Graduate Scholarship
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The synthesis of a beta-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 beta-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 beta-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.
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