Comparison of 1-(1-naphthyl)ethylcarbamate derivatives of a carbohydrate bonded chiral stationary phase

J Chromatogr A. 1995 Mar 31;695(2):185-93. doi: 10.1016/0021-9673(94)01164-a.

Abstract

New chiral stationary bonded phases (CSPs) based on derivatized malto-oligosaccharides are reported. Chiral separations are reported for 3,5-dinitrobenzoyl-derivatized amines and amino acids as well as some 3,5-dinitrophenylcarbamoylated alcohols. These new CSPs incorporate a 1-(1-naphthyl)ethylcarbamate (NEC) moiety which introduces additional stereogenicity and provides a useful probe for investigating chiral recognition. The elution order, when known, was dependent upon the configuration of the NEC substituent; that is, the S enantiomers were retained longest on the S column and the R enantiomers were retained longest on the R column. Elution order from the RS column, when known, was the same as that observed for the S column. In most cases, retention correlated with bonded ligand concentration on the silica substrate. In general, the best enantioselectivities and resolution were obtained on the S column.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alcohols / analysis
  • Amines / analysis
  • Amino Acids / analysis
  • Carbamates / chemistry*
  • Carbohydrates / chemistry*
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods*
  • Esters / analysis
  • Naphthalenes / chemistry*

Substances

  • Alcohols
  • Amines
  • Amino Acids
  • Carbamates
  • Carbohydrates
  • Esters
  • Naphthalenes