Abstract
The use of norbornene units to induce the formation of β-sheet and β-turn type structures in peptides is discussed. The norbornene unit is readily prepared by a desymmetrization reaction and is easily incorporated into a peptide chain. Depending upon the exact nature of the norbornene unit, it is possible to form structures which resemble parallel β-sheets, antiparallel β-sheets or β-turns. Similar peptide analogues incorporating a cis-2-amino-cyclopropane carboxylic acid unit can also be prepared. As an illustration of the application of this chemistry, a short, asymmetric synthesis of conformationally constrained metalloprotease inhibitors is presented. Copyright © 2000 European Peptide Society and John Wiley & Sons, Ltd.
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