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

Doralyn S. Dalisay, Tim Quach, Gillian N. Nicholas, Tadeusz F. Molinski

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22 Citations (Scopus)

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 π- π* 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.

Original languageEnglish
Pages (from-to)4367-4371
Number of pages5
JournalAngewandte Chemie - International Edition
Volume48
Issue number24
DOIs
Publication statusPublished - 2 Jun 2009
Externally publishedYes

Keywords

  • Circular dichroism
  • Liposomes
  • Natural products
  • Peroxides
  • Polyketides

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