β2,2-Aminoxy Acids: A New Building Block for Turns and Helices
- 1 August 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (34), 9966-9967
- https://doi.org/10.1021/ja026966n
Abstract
The conformational properties of peptides 1-4 built from 3-aminoxy-2,2-dimethyl-propionic acid, a β2,2-aminoxy acid, were investigated by NMR spectroscopy and X-ray crystallography. A novel β N-O turn involving a nine-membered-ring intramolecular hydrogen bond between NHi+2 and COi was formed in diamides 1 and 2, which was further stabilized by another six-membered-ring intramolecular hydrogen bond between NHi+2 and NOi+1. Triamides 3 and 4 displayed a well-defined helical structure featuring two consecutive β N-O turns. The X-ray structure of 4 revealed that the amide carbonyl group at position i+2 was twisted +65.9° from that at i position, suggesting a novel 1.79 helix. Therefore, β2,2-aminoxy acid can be used as a new building block for turns and helices. Copyright © 2002 American Chemical Society.link_to_subscribed_fulltexKeywords
This publication has 16 references indexed in Scilit:
- γ2-,γ3-, andγ2,3,4-Amino Acids, Coupling toγ-Hexapeptides: CD Spectra, NMR Solution and X-ray Crystal Structures ofγ-PeptidesChemistry – A European Journal, 2002
- Parallel Sheet Secondary Structure in γ-PeptidesJournal of the American Chemical Society, 2001
- β-Peptides: From Structure to FunctionChemical Reviews, 2001
- Design, Synthesis, NMR-Solution and X-Ray Crystal Structure ofN-Acyl-γ-dipeptide Amides That Form aβII′-Type TurnHelvetica Chimica Acta, 2001
- Preparation and determination of X-ray-crystal and NMR-solution structures of γ2,3,4-peptidesChemical Communications, 2001
- Theoretical Study of Peptides Formed by Aminoxy AcidsJournal of the American Chemical Society, 1999
- Novel Turns and Helices in Peptides of Chiral α-Aminoxy AcidsJournal of the American Chemical Society, 1999
- Design of Secondary Structures in Unnatural Peptides: Stable Helical γ-Tetra-, Hexa-, and Octapeptides and Consequences of α-SubstitutionJournal of the American Chemical Society, 1998
- γ‐Peptides Forming More Stable Secondary Structures than α‐Peptides: Synthesis and helical NMR‐solution structure of the γ‐hexapeptide analog of H‐(Val‐Ala‐Leu)2‐OHHelvetica Chimica Acta, 1998
- Vinylogous polypeptides: an alternative peptide backboneJournal of the American Chemical Society, 1992