Document Detail


Conformation and Chiral Effects in α,β,α-Tripeptides.
MedLine Citation:
PMID:  22775557     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Short α,β,α-tripeptides comprising a central chiral trisubstituted β(2,2,3)*-amino acid residue form unusual γ-turns and δ-turns in CDCl(3) and DMSO-d(6) solutions but do not form β-turns. Thermal coefficients of backbone amide protons, 2D-NMR spectra, and molecular modeling revealed that these motifs were strongly dependent on the configuration (chiral effect) of the central β-amino acid residue within the triad. Accordingly, SSS tripeptides adopted an intraresidual γ-turn like (C6) arrangement in the central β-amino acid, whereas SRS diastereomers preferred an extended δ-turn (C9) conformation. A different SRS-stabilizing bias was observed in the crystal structures of the same compounds, which shared the extended δ-turn (C9) found in solution, but incorporated an additional extended β-turn (C11) to form an overlapped double turn motif.
Authors:
Carlos J Saavedra; Alicia Boto; Rosendo Hernández; José Ignacio Miranda; Jesus M Aizpurua
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-7-10
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-7-10     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Instituto de Productos Naturales y Agrobiología del CSIC , Avda. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain.
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