NDLI: The Effect of Backbone Stereochemistry on the Folding of Acyclic $β^{2, 3}-Aminoxy$ Peptides

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The Effect of Backbone Stereochemistry on the Folding of Acyclic $β^{2, 3}-Aminoxy$ Peptides

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Zhang, Yu-hui Song, Kesheng Zhu, Nian-yong Yang, Dan
Description	Author Affiliation: Zhang YH ( Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.)
Abstract	As a new type of foldamer, β-aminoxy peptides have the ability to adopt novel β NO turns or β NO helices in solution. Herein, we describe a new subclass of β-aminoxy peptide, that is, peptides of acyclic $β^{2, 3}-aminoxy$ acids $(NH_{2}OCHR_{1}CHR_{2}COOH),$ in which the presence of two chiral centers provides insight into the effect of backbone stereochemistry on the folding of β-aminoxy peptides. Acyclic $β^{2, 3}-aminoxy$ peptides with syn and anti configurations have been synthesized and their conformations investigated by NMR, IR, and circular dichroism (CD) spectroscopic, and X-ray crystallographic analysis. The β NO turns or β NO helices, which feature nine-membered rings with intramolecular hydrogen bonds and have been identified previously in peptides of $β^{3}-$ and $β^{2, 2}-aminoxy$ acids, are also predominantly present in the acyclic $β^{2, 3}-aminoxy$ peptides with a syn configuration and NO bonds gauche to the $C_{α}C_{β}$ bonds in both solution and the solid state. In the acyclic $β^{2, 3}-aminoxy$ peptides with an anti configuration, an extended strand (i.e., non-hydrogen-bonded state) is found in the solid state, and several conformations including non-hydrogen-bonded and intramolecular hydrogen-bonded states are present simultaneously in nonpolar solvents. These results suggest that the backbone stereochemistry does affect the folding of the acyclic $β^{2, 3}-aminoxy$ peptides. Theoretical calculations on the conformations of model acyclic $β^{2, 3}-aminoxy$ peptides with different backbone stereochemistry were also conducted to elucidate structural characteristics. Our present work may provide useful guidelines for the design and construction of new foldamers with predicable structures.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	2
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-01-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Models, Theoretical Peptides Chemistry Crystallography, X-Ray Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Protein Structure, Secondary Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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