Document Detail

On Chirality Measures of α-Amino Acids.
MedLine Citation:
PMID:  22587304     Owner:  NLM     Status:  Publisher    
To measure molecular chirality, the molecule is treated as a finite set of points in the Euclidean R3 space supplemented by k properties, p(i)1, p(i)2, ..., p(i)k assigned to i-th atom, which constitute a point in the Property Pk space. Chirality measures are described as the distance between a molecule and its mirror image minimized over all its arbitrary orientation-preserving isometries in the R3Pk Cartesian product space. Following this formalism, different chirality measures can be estimated by taking into consideration different sets of atomic properties. Here, for α-amino acid zwitterionic structures taken from Cambridge Structural Database and for all 1684 neutral conformers of 19 biogenic α-amino acid molecules, except glycine and cystine, found at the B3LYP/6-31G** level, chirality measures have been calculated by CHIMEA program written in this project. It is demonstrated that there is a significant correlation between the measures determined for the α-amino acid zwitterions in crystals and the neutral forms in the gas phase. Performance of the studied chirality measures with changes of the basis set and computation method was also checked. An exemplary QSAR application of the chirality measures was presented by an introductory model for the benchmark Cramer dataset of steroidal ligands of the sex-hormone binding globulin.
Michał H Jamróz; Joanna Ewa Rode; Sławomir Ostrowski; Piotr F J Lipiński; Jan Czeslaw Dobrowolski
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-5-15
Journal Detail:
Title:  Journal of chemical information and modeling     Volume:  -     ISSN:  1549-960X     ISO Abbreviation:  -     Publication Date:  2012 May 
Date Detail:
Created Date:  2012-5-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101230060     Medline TA:  J Chem Inf Model     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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