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Discrimination of enantiomers of α-amino acids by chiral derivatizing reagents from trans-1,2-diaminocyclohexane

✍ Scribed by Magdalena Kaik; Jadwiga Gajewy; Jakub Grajewski; Jacek Gawronski

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
219 KB
Volume
20
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

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.

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## Abstract Enantiomeric discrimination of chiral primary amines was performed by both reversed‐phase HPLC and normal‐phase HPLC after labeling with a chiral fluorescent derivatization reagent, (1__R__,2__R__)‐ and (1__S__,2__S__)‐__trans__‐2‐(2,3‐anthracenedicarboximido)cyclohexanecarbonyl chlorid