Amplification of the Cotton effect of a single chromophore through liposomal ordering-stereochemical assignment of plakinic acids I and J

Angew Chem Int Ed Engl. 2009;48(24):4367-71. doi: 10.1002/anie.200900888.

Abstract

A dramatic effect is observed when acyclic N-(2-naphthamides) of medium-chain 1-amino-2-methylalkanes are partially ordered with the help of liposomes: the Cotton effect arising from pi-pi* transitions of the terminal naphthamide chromophor is enormously enhanced. This effect was exploited to assign the configuration of new polyketide peroxides such as 1 from the sponge Plakortis halichondroides.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetates / chemistry*
  • Animals
  • Circular Dichroism
  • Liposomes / chemistry*
  • Peroxides / chemistry*
  • Plakortis / chemistry
  • Stereoisomerism

Substances

  • Acetates
  • Liposomes
  • Peroxides
  • plakinic acid I
  • plakinic acid J