Configuration of heptopyranoside and heptofuranoside side chains: 2-anthroate, a powerful chromophore for exciton coupled CD

Chirality. 1997;9(7):699-712. doi: 10.1002/(SICI)1520-636X(1997)9:7<699::AID-CHIR11>3.0.CO;2-I.

Abstract

The absolute configuration of the acyclic side chain of heptopyranosides and heptofuranosides was determined by exciton coupled CD, employing the strongly fluorescent 2-anthroate chromophore. The usage of this chromophore offers significant improvements over previous chemical and spectroscopic procedures since its intense fluorescence greatly facilitates the isolation and HPLC purification at the nanogram scale. The large amplitudes of the bisignate spectra allow CD manipulations in the 1 x 10(-7) M range.

Publication types

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

MeSH terms

  • Anthracenes / chemistry
  • Carbohydrate Conformation
  • Chromogenic Compounds
  • Circular Dichroism
  • Fluorescent Dyes
  • Heptoses / chemistry*
  • Lipopolysaccharides / chemistry
  • Stereoisomerism

Substances

  • Anthracenes
  • Chromogenic Compounds
  • Fluorescent Dyes
  • Heptoses
  • Lipopolysaccharides