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Ring‐Opening Cross‐Metathesis (ROCM) as a Novel Tool for the Ligation of Peptides
Author(s) -
Michaelis Simon,
Blechert Siegfried
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601183
Subject(s) - salt metathesis reaction , chemistry , combinatorial chemistry , peptide , metathesis , ligation , olefin fiber , fluorescence , catalysis , olefin metathesis , stereochemistry , organic chemistry , biochemistry , biology , polymerization , physics , microbiology and biotechnology , quantum mechanics , polymer
The development of ring‐opening cross‐metathesis (ROCM) as a novel tool for the site‐specific ligation of peptide units is reported. The resulting structural units at the site of ligation resulting from ROCM resemble proline as well as other known β‐turn stabilising structural units. ROCM under mild reaction conditions between a variety of peptides bearing a cyclic olefin with amino acids or peptides results in high yields. The peptidic cross‐partners for metathesis are equipped with double bonds via the N and the C terminus and the side chain, respectively, to allow the synthesis of linear as well as non‐linear and branched peptides. The ligation in this manner succeeds with low catalyst loadings, with no need for any excess of one reaction partner and with a high compatibility with a wide range of functional groups. Furthermore, the stereochemical outcome of the ROCM can easily be controlled by using a Hoveyda‐type chiral catalyst. Fluorescence labelling of peptides is possible in the same manner when using a cyclic olefin equipped with a fluorescence marker.