期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 350, 期 11-12, 页码 1661-1675出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800149
关键词
disulfide bond surrogate; olefin metathesis; peptides; peptidomimetics; ring-closing metathesis; turn mimic
资金
- Israel Science Foundation
- Kahanoff Founadion
- Marc Rich Foundation
- Marie Curie International Reintegration [MIRG-CT-2007-046374]
This review is intended to cover the applications of olefin metathesis, with its variations, to the synthesis and manipulation of peptides and peptidomimetics. The examples presented here emphasize the use of metathesis in several aspects of peptides and peptidomimetics, from amino acid synthesis, design and synthesis of secondary structure elements, and manipulation of pharmaceutically active peptides and peptidomimetics to improve their stability and activity. These examples testify to the power of the ruthenium-based catalysts, which are particularly useful in the synthesis of complex molecules such as peptides, due to their high stability in various media, high chemoselectivity, and tolerance to a variety of functional groups that decorate the peptide side chains. Another observation one could make from surveying these studies is that ring-closing metathesis (RCM) is the most used variation of olefin metathesis in these fields. Finally, metathesis, which leads to the formation of carbon-carbon bonds with various hybridization states, i.e., alkyne, alkene, and alkane allows for great diversity and flexibility in the synthesis leading to novel structures and function properties. Unarguably, metathesis is a fascinating reaction that continues to have its impact in various fields including peptides and peptidomimetics.
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