Premium
Amplification of the Cotton Effect of a Single Chromophore through Liposomal Ordering—Stereochemical Assignment of Plakinic Acids I and J
Author(s) -
Dalisay Doralyn S.,
Quach Tim,
Nicholas Gillian N.,
Molinski Tadeusz F.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900888
Subject(s) - liposome , chromophore , polyketide , stereochemistry , chemistry , amino acid , single chain , sponge , combinatorial chemistry , organic chemistry , biochemistry , biology , genetics , botany , biosynthesis , enzyme , antibody
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.