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DOI: 10.1039/A800653I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 1651-1658

Linear oligopeptides. Part 406.1 Helical screw sense of peptide molecules: the pentapeptide system (Aib)4/L-Val[L-(αMe)Val] in solution

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Barbara Pengo, Fernando Formaggio, Marco Crisma, Claudio Toniolo, Gian Maria Bonora, Quirinus B. Broxterman, Johan Kamphuis, Michele Saviano, Rosa Iacovino, Filomena Rossi and Ettore Benedetti

Abstract

A variety of N[hair space] α-blocked pentapeptide esters, each containing four helicogenic, achiral α-aminoisobutyric acid residues and one chiral L-valine or C[hair space] α-methyl-L-valine residue in the N-terminal, internal or C-terminal position of the sequence, have been synthesized by solution methods and fully characterized. The results of a solution conformational analysis, performed by using FTIR absorption and 1H NMR techniques, favour the conclusion that all of the pentapeptides examined fold into a 310-helical structure. In addition, a CD study of the N[hair space] α-para-bromobenzoylated peptides strongly supports the view that the prevailing screw sense of the 310-helical structure that is formed is strongly dependent upon the position in the sequence of the single chiral C[hair space] α-tri- or C[hair space] α-tetrasubstituted α-amino acid.

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