10-Helical conformations in oxetane beta-amino acid hexamers

Authors
Claridge, TDW Goodman, JM Moreno, A Angus, D Barker, SF Taillefumier, C Watterson, MP Fleet, GWJ
Citation
Tdw. Claridge et al., 10-Helical conformations in oxetane beta-amino acid hexamers, TETRAHEDR L, 42(25), 2001, pp. 4251-4255
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
25
Year of publication
2001
Pages
4251 - 4255
Database
ISI
SICI code
0040-4039(20010618)42:25<4251:1CIOBA>2.0.ZU;2-B
Abstract
The first structural investigations were undertaken on a P-hexapeptide 7 in which the peptide backbone is constrained by cis-substituted oxetane rings . Detailed NMR studies in CDCl3 and C6D6 together with molecular mechanics conformational analysis identify a well-defined left-handed helical structu re stabilised by 10-membered hydrogen-bonded rings. Comparison with two rel ated hexapeptides 8 and 9 suggests a similar structural preference for thes e systems. (C) 2001 Elsevier Science Ltd. All rights reserved.