Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 9, Pages 4270-4277Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4001542
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Funding
- Science Foundation Ireland [PIYRA 07/YI2/I1052]
- Trinity College
- L'Oreal UNESCO For Women in Science Fellowship
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The sequential combination of native chemical ligation and thiol-ene radical chemistry (NCL-TEC) on the resulting cysteine thiol has been investigated as a methodology for rapidly accessing functionalized peptides. Three sequential cycles of native chemical ligation and subsequent thiyl radical reactions (including a free-radical-mediated desulfurization reaction) were carried out on a peptide backbone demonstrating the iterative nature of this process. The versatility of the thiyl radical reaction at cysteine was demonstrated through the introduction of a number of different side chains including an amino acid derivative, a carbohydrate group, and an alkyl azide. Conditions were developed that allowed the sequential NCL-TEC process to proceed in high yield.
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