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

• Type: Article in International Scientific Journal
• Date: 2017

Authors

Sampaio Dias, IE (Author) Other; Sousa, CAD (Author) Other; Silva Reis, SC (Author) Other; Ribeiro, S (Author) Other; Garcia Mera, X (Author) Other; Rodriguez Borges, JE (Author) FCUP

Journal

Title: Organic and Biomolecular Chemistry

Vol. 15

Pages: 7533-7542

ISSN: 1477-0520

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 10 Citations

Scopus - 10 Citations

Other information

Authenticus ID: P-00N-1ZR

DOI: 10.1039/c7ob01544e

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10