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

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

Author information

1
Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA.

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.

PMID:
19437515
PMCID:
PMC2872062
DOI:
10.1002/anie.200900888
[Indexed for MEDLINE]
Free PMC Article

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