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Reversed-phase chromatographic resolution of N-(3,5-dinitrobezoyl)- α-amino acids on chiral stationary phases

✍ Scribed by William H. Pirkle; Myung Ho Hyun

Book ID
104146626
Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
551 KB
Volume
322
Category
Article
ISSN
1873-3778

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✦ Synopsis

The enantiomers of N-(3,5_dinitrobenzoyl)-a-amino acids are readily separated by reversed-phase chromatography on chiral stationary phases. Lipophilic interactions are quite important and largely determine the relative contributions of two competing "opposite sense" chiral recognition processes. Selectivities are fairly high and, on chiral phase 2a, derived from (&)-N-(1 l-triethoxysilyhmdecanoyl)cyclohexyl(6,7-dimethyl-1-naphthyl)methylamine, are adequate for preparative separations as well as analytical separations. The (nenantiomers consistently elute last from the (R)-2a column. Chiral recognition models are proposed to accommodate the observed separability factors and elution orders.

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