Native Chemical Ligation,Thiol-Ene Click: A Methodology for the Synthesis of Functionalized Peptides

作者：Markey Lyn; Giordani Silvia^*; Scanlan Eoin M

来源：Journal of Organic Chemistry, 2013, 78(9): 4270-4277.

DOI：10.1021/jo4001542

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.

• 出版日期2013-5-3