| Conformation and Chiral Effects in α,β,α-Tripeptides. | |
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MedLine Citation:
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PMID: 22775557 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Carlos J Saavedra; Alicia Boto; Rosendo Hernández; José Ignacio Miranda; Jesus M Aizpurua |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-7-10 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2012 Jul |
Date Detail:
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Created Date: 2012-7-10 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Instituto de Productos Naturales y Agrobiología del CSIC , Avda. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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