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Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis

2008; Wiley; Volume: 47; Issue: 44 Linguagem: Inglês

10.1002/anie.200803523

1521-3773

Jin Chen, Qian Wan, Yu Yuan, Jianglong Zhu, Samuel J. Danishefsky,

Click Chemistry and Applications

A Val-uable link: The title transformation is achieved by a two-step ligation, radical-based desulfurization strategy (see scheme; NCL=native chemical ligation). After S→N acyl transfer, in which the acyl acceptor is a γ-thiol valine derivative, and site-specific dethiolation, a valine residue appears at the site of ligation. This method accomplishes ligations at Thr-Val and Pro-Val sites, and allows successful ligation of glycopeptide fragments. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.