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Solid‐Phase Synthesis of Peptides Containing α,β‐Didehydroamino Acids
Author(s) -
Royo Miriam,
Jiménez Jose C.,
LópezMacià Angel,
Giralt Ernest,
Albericio Fernando
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:1<45::aid-ejoc45>3.0.co;2-v
Subject(s) - chemistry , carbodiimide , reagent , peptide bond , peptide synthesis , solid phase synthesis , combinatorial chemistry , peptide , amino acid , organic chemistry , phase (matter) , side chain , biochemistry , polymer
α,β‐Didehydroamino acids are frequently encountered in natural peptides with important biological activity. Herein, we report a mild and convenient method for the preparation of peptides containing α,β‐didehydroamino acids, where solid‐phase techniques are used both for elongation of the peptide chain and formation of the double bond. This bond is formed through a β‐elimination reaction, using a water soluble carbodiimide as the activating reagent of the hydroxyl function, and catalyzed by CuCl.