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

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...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 36; pp. 7533 - 7542
Main Authors Sampaio-Dias, Ivo E., Sousa, Carlos A. D., Silva-Reis, Sara C., Ribeiro, Sara, Garcia-Mera, Xerardo, Rodriguez-Borges, Jose E.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANALOGS
AMINES
AMIDATION
RACEMIZATION
AMIDE BOND FORMATION
PROLINE
CARBOXYLIC-ACIDS
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Summary: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.
Bibliography:FCT
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01544e