Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power

Org Biomol Chem. 2004 Dec 21;2(24):3602-7. doi: 10.1039/b411110a. Epub 2004 Nov 9.

Abstract

The non-empirical assignment of the absolute configuration of (-)-naringenin, the aglycone of (-)-naringin, a flavanone glycoside abundant in the albedo of immature grapefruits and showing several interesting biological properties, has been approached by two different methods: (a) the exciton analysis of the circular dichroism (CD) spectrum and (b) the ab initio calculation of the optical rotatory power. Both the methods indicate the configurational correlation (-)/(S), as empirically suggested by Gaffield. A comparison of advantages and limitations of the two methods of analysis is also presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • Flavanones / chemistry*
  • Flavanones / isolation & purification
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Optical Rotation
  • Stereoisomerism

Substances

  • Flavanones
  • naringenin