Long-range stereo-relay: relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters

J Am Chem Soc. 2004 Aug 18;126(32):9944-5. doi: 10.1021/ja047741a.

Abstract

The relative and absolute configurations of long-chain syn- and anti-1,5-, 1,7- and 1,9-glycols were determined from exciton-coupled circular dichroism (ECCD) of the corresponding bis-5-(4'-carboxyl)-5,10,15,20-tetraphenylporphyrin esters measured in uniform (phi = 26 nm), unilamellar liposomes. Long-range transmission of configuration by ECCD is made possible through partial ordering of glycol ester-lipid molecules by liposomal bilayers.

Publication types

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

MeSH terms

  • Circular Dichroism
  • Esters / chemistry
  • Glycols / chemistry*
  • Liposomes / chemistry
  • Molecular Conformation
  • Porphyrins / chemistry*
  • Stereoisomerism

Substances

  • Esters
  • Glycols
  • Liposomes
  • Porphyrins