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

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.

journal_name

Chirality

journal_title

Chirality

authors

Kaik M,Gajewy J,Grajewski J,Gawronski J

doi

10.1002/chir.20435

subject

Has Abstract

pub_date

2008-03-01 00:00:00

pages

301-6

issue

3-4

eissn

0899-0042

issn

1520-636X

journal_volume

20

pub_type

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