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  • Title: Discrimination of enantiomers of alpha-amino acids by chiral derivatizing reagents from trans-1,2-diaminocyclohexane.
    Author: Kaik M, Gajewy J, Grajewski J, Gawronski J.
    Journal: Chirality; 2008 Mar; 20(3-4):301-6. PubMed ID: 17600850.
    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 1H NMR signals are observed for enantiomers of suitably protected alpha-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.
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