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Abstract
Cyclisation reactions on pentapeptides containing the turn promoting residues Gly and Pro are investigated. Although the cyclisation reaction is fast, solvent-dependent mixtures of cyclic penta- and decapeptides are observed. NMR studies suggest a strong dependence of the monomer/dimer ratio on the cis-trans isomerisation found in linear and cyclic peptides. The critical influence on ring closure of a cis Xaa-Pro peptide bond conformation is demonstrated by using the cis peptide bond-inducing residue 2,2-dimethyl-1,3-thiazolidine-4 carboxylic acid (Dmt, pseudo-proline) as proline substitute. The results shed new light on the role of cis-trans isomerisation in pentapeptide cyclisation.
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