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Discrimination of enantiomers of α‐amino acids by chiral derivatizing reagents from trans ‐1,2‐diaminocyclohexane
Author(s) -
Kaik Magdalena,
Gajewy Jadwiga,
Grajewski Jakub,
Gawronski Jacek
Publication year - 2008
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20435
Subject(s) - chemistry , enantiomer , chiral derivatizing agent , substituent , reagent , chirality (physics) , imide , stereochemistry , amino acid , amide , covalent bond , organic chemistry , chiral column chromatography , nambu–jona lasinio model , physics , biochemistry , quark , chiral symmetry breaking , quantum mechanics
New chiral derivatizing reagents (CDAs) derived from trans ‐1,2‐diaminocyclohexane, having an electron‐deficient aromatic substituent (either an aromatic imide or 3,5‐dinitrobenzamide) and rigid structure (either an amide or a urea linker), are reported. Significant shift differences of diastereotopic protons in the 1 H NMR signals are observed for enantiomers of suitably protected α‐amino acids, linked to CDA by a covalent bond. A simple, general model rationalizing the observed enantiomer discrimination and based on semiempirical conformational search is presented. Chirality, 2008. © 2007 Wiley‐Liss, Inc.