Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis

A highly efficient, two-step, one-pot synthetic strategy for amides and peptides was developed by employing ynamides as novel coupling reagents under extremely mild reaction conditions. The ynamides not only are effective for simple amide and dipeptide synthesis but can also be used for peptide segm...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-10, Vol.138 (40), p.13135-13138
Main Authors: Hu, Long, Xu, Silin, Zhao, Zhenguang, Yang, Yang, Peng, Zhiyuan, Yang, Ming, Wang, Changliu, Zhao, Junfeng
Format: Article
Language:English
Subjects:
amides
carboxylic acids
peptides
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Summary:A highly efficient, two-step, one-pot synthetic strategy for amides and peptides was developed by employing ynamides as novel coupling reagents under extremely mild reaction conditions. The ynamides not only are effective for simple amide and dipeptide synthesis but can also be used for peptide segment condensation. Importantly, no racemization was detected during the activation of chiral carboxylic acids. Excellent amidation selectivity toward amino groups in the presence of −OH, −SH, −CONH2, ArNH2, and the NH of indole was observed, making the protection of these functional groups unnecessary in amide and peptide synthesis.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.6b07230