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Preparation and C‐Alkylation of Peptides with Aminomalonate Building Blocks
Author(s) -
Bossler Hans G.,
Waldmeier Pius,
Seebach Dieter
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199404391
Subject(s) - alkylation , tripeptide , peptide , alkyl , halide , cleavage (geology) , chemistry , combinatorial chemistry , stereochemistry , peptide synthesis , organic chemistry , biochemistry , biology , catalysis , paleontology , fracture (geology)
The preparation of a whole series of peptides —starting from a single precursor—can be achieved with readily available tripeptides such as 1 (R = H). They contain aminomalonate building blocks which can be alkylated with alkyl halides and Michael acceptors under basic conditions in good to excellent yields. By cleavage of the benzyloxycarbonyl group, peptide derivatives 1 , R = alkyl, etc. are obtained, which can then be further modified. Such peptide series are of particular interest, for example, for screenings (“peptide libraries”).