Document Detail


Secondary Structure of Short beta-Peptides as the Chiral Expression of Monomeric Building Units: a Rational and Predictive Model.
MedLine Citation:
PMID:  23030251     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Chirality of the monomeric residues controls and determines the prevalent folding of small oligopeptides (from di- to tetramers) composed of the 2-aminocyclobutane-1-carboxylic acid (ACBA) derivatives with the same or different absolute and relative configuration. The cis-form of the monomeric ACBA gives rise to two conformers, namely Z6 and Z8, while the trans-form manifests uniquely as an H8 structure. By combining these subunits in oligo- and polypeptides, their local structural preference remains thus allowing the rational design of new short foldamers. A lego-type molecular architecture evolves; the overall looking depends only on the conformational properties of the structural building units. A versatile and efficient method to predict the backbone folds of designed cyclobutane beta-peptides is based on QM calculations. Predictions are corroborated by high-resolution NMR studies on selected stereoisomers most of them being new foldamers that have been synthesized and characterized for the first time. Thus, the chiral expression of monomeric building units results in the defined secondary structures of small oligomers. As result of this study, a new set of chirality controlled foldamers are provided to probe as biocompatible biopolymers.
Authors:
Esther Gorrea; Gabor Pohl; Pau Nolis; Sergio Celis; Kepa K Burusco; Vicenç Branchadell; András Perczel; Rosa M Ortuño
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-3
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-3     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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