Open AccessThe Chirality Chain in Valine: How the Configuration at the C α Position through the O cis C′C α N Torsional System Leads to Distortion of the Planar Group C α C′(O cis )O trans to a Flat Tetrahedron
Author(s) -
Brunner Henri,
Tsuno Takashi
Publication year - 2018
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201800137
Subject(s) - chirality (physics) , tetrahedron , crystallography , chemistry , planar chirality , flattening , stereochemistry , molecular geometry , tripeptide , position (finance) , physics , molecule , enantioselective synthesis , amino acid , quantum mechanics , biochemistry , chiral symmetry breaking , organic chemistry , astronomy , nambu–jona lasinio model , quark , catalysis , finance , economics
Solid‐state structures, based on a Cambridge Structural Database (CSD) search, show that there is a C α N/C′O cis attraction in the torsional system O cis C′C α N of valine, causing a chirality chain. The C α configuration controls the chirality of the rotation around the C′−C α bond, which in turn induces a distortion of the planar unit C α 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 α bond as well as stretching and flattening of the tetrahedron. The molecular property C α N/C′O cis attraction of valine is maintained in its di‐ and tripeptides.