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Rationally Designed Bicyclic Lactams Control Different Turn Motifs and Folding Patterns in Hexapeptide Mimics (2000)

Belvisi, Laura ; Gennari, Cesare ; Madder, Annemieke ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 695-699

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ISSN: 1434-193X

Keywords: Reverse-turn mimics ; γ-Turns ; β-Turns ; β-Hairpins ; Peptides ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---Conformational analysis of N-acetylated hexapeptide mimics incorporating a bicyclic lactam (1-4) was carried out by a combination of 1H-NMR spectroscopy, IR spectroscopy, and computer modeling. The nature of the bicyclic lactam determines the turn motifs and the folding patterns of these constrained peptides. The (5,6)-bicyclic lactam derivatives 1 and 2, characterized by a type-II' β-turn (C=O3···H6-N), are very compact intramolecularly H-bonded structures. The (5,7)-bicyclic lactam derivative 3, characterized by an inverse γ-turn (C=O4···H6-N), is a quite flexible “tweezer-like” structure.

Additional Material: 4 Ill.

Type of Medium: Electronic Resource

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