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Highly Efficient One-Pot Assemble of Peptides by Double Chemoselective Coupling

Abstract

This work describes a methodological advance in the solution-phase peptide synthesis by the development of a convenient and operational protocol to synthesize oligopeptides in a one-pot three-step cascade fashion way, in which two peptide bonds are introduced chemoselectively. Tri- to hexapeptides were obtained in high global yields (80-95%) without virtually no epimerization determined by HPLC. The methodology herein described represents a faster, easier and milder approach to the synthesis of peptides and operates at equimolar amounts. This protocol comprises the formation of primary and secondary 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.

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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, Accepted Manuscript
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    Highly Efficient One-Pot Assemble of Peptides by Double Chemoselective Coupling

    I. E. Sampaio-Dias, C. A. Sousa, S. C. Silva-Reis, S. Ribeiro, X. Garcia-Mera and J. E. Rodriguez-Borges, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB01544E

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