The Chirality Chain in Valine: How the Configuration at the C-alpha Position through the OcisC ' C alpha N Torsional System Leads to Distortion of the Planar Group C alpha C '(O-cis)O-trans to a Flat Tetrahedron

Brunner, Henri and Tsuno, Takashi (2018) The Chirality Chain in Valine: How the Configuration at the C-alpha Position through the OcisC ' C alpha N Torsional System Leads to Distortion of the Planar Group C alpha C '(O-cis)O-trans to a Flat Tetrahedron. CHEMISTRYOPEN, 7 (9). pp. 696-700. ISSN 2191-1363,

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Abstract

Solid-state structures, based on a Cambridge Structural Data-base (CSD) search, show that there is a C alpha N/C'O-cis attraction in the torsional system OcisC'C alpha N of valine, causing a chirality chain. The C-alpha configuration controls the chirality of the rotation around the C'-C-alpha bond, which in turn induces a distortion of the planar unit C alpha C'(O)O to a flat asymmetric tetrahedron. Conformational "reactions" take place in an energy profile with respect to clockwise and counterclockwise rotation around the C'- C-alpha bond as well as stretching and flattening of the tetrahedron. The molecular property C alpha N/C'O-cis attraction of valine is maintained in its di- and tripeptides.

Item Type: Article
Uncontrolled Keywords: CAMBRIDGE STRUCTURAL DATABASE; CRYSTAL-STRUCTURES; amino acids; chirality; conformation; peptides; valine
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 09 Jan 2020 07:13
Last Modified: 09 Jan 2020 07:13
URI: https://pred.uni-regensburg.de/id/eprint/13942

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