J Org Chem. 2003 Dec 12;68(25):9541-53.

Synthesis of 3-aminolactams as X-Gly constrained pseudodipeptides and conformational study of a Trp-Gly surrogate.

Ecija M, Diez A, Rubiralta M, Casamitjana N, Kogan MJ, Giralt E.

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Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain, and Parc Científic de Barcelona, c/ Josep Samitier, 1-5, 08028-Barcelona, Spain.

Abstract

3-Amino-delta-valerolactams trans-11a-c were synthesized through conjugate addition and Curtius rearrangement and converted into Fmoc-[Trp-Gly], Fmoc-[Ile-Gly], and Fmoc-[Phe-Gly] pseudodipeptides. Conformational analyses of tripeptide analogues Ac-[Trp-Gly]-Leu-NH(2) 17a and 17b by NMR experiments and molecular modeling calculations showed that diastereomer 17a adopted a gamma-turn/distorted type II beta-turn structure, whereas diastereomer 17b adopted mainly a gamma-turn structure.

PMID:: 14656078; [PubMed - indexed for MEDLINE]

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