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Issue 36, 2017
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Highly efficient one-pot assembly of peptides by double chemoselective coupling

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Abstract

This study describes a methodological advancement in solution-phase peptide synthesis via the development of a convenient and operational protocol to synthesize oligopeptides in a one-pot three-step cascade method, in which two peptide bonds are introduced chemoselectively. Tri- to hexapeptides were obtained in high global yields (80–95%) with virtually no epimerization as determined via HPLC. The methodology described herein represents a faster, easier and milder approach to the synthesis of peptides, and it operates at equimolar amounts. This protocol comprises the formation of secondary and tertiary amides and is compatible with Z, Boc and Fmoc N-protecting groups as well as the use of D/L and non-proteinogenic amino acids.

Graphical abstract: Highly efficient one-pot assembly of peptides by double chemoselective coupling

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Publication details

The article was received on 26 Jun 2017, accepted on 04 Aug 2017 and first published on 04 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01544E
Citation: Org. Biomol. Chem., 2017,15, 7533-7542
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    Highly efficient one-pot assembly of peptides by double chemoselective coupling

    I. E. Sampaio-Dias, C. A. D. Sousa, S. C. Silva-Reis, S. Ribeiro, X. García-Mera and J. E. Rodríguez-Borges, Org. Biomol. Chem., 2017, 15, 7533
    DOI: 10.1039/C7OB01544E

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