Conformational analysis of N-acetylated hexapeptide mimics incorporating a bicyclic lactam (1-4) was carried out by a combination of H-1-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' beta-turn (C=O-3... H-6-N), are very compact intramolecularly H-bonded structures. The (5,7)-bicyclic lactam derivative 3, characterized by an inverse gamma-turn (C=O-4... H-6-N), is a quite flexible "tweezer-like" structure.
Rationally designed bicyclic lactams control different turn motifs and folding patterns in hexapeptide mimics / L. Belvisi, C.M.A. Gennari, A. Madder, A. Mielgo, D. Potenza, C. Scolastico. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2000:5(2000), pp. 695-699. [10.1002/(SICI)1099-0690(200003)2000:5<695::AID-EJOC695>3.0.CO;2-V]
Rationally designed bicyclic lactams control different turn motifs and folding patterns in hexapeptide mimics
L. BelvisiPrimo
;C.M.A. GennariSecondo
;D. PotenzaPenultimo
;C. ScolasticoUltimo
2000
Abstract
Conformational analysis of N-acetylated hexapeptide mimics incorporating a bicyclic lactam (1-4) was carried out by a combination of H-1-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' beta-turn (C=O-3... H-6-N), are very compact intramolecularly H-bonded structures. The (5,7)-bicyclic lactam derivative 3, characterized by an inverse gamma-turn (C=O-4... H-6-N), is a quite flexible "tweezer-like" structure.
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