Amplification of the Cotton Effect of a Single Chromophore through Liposomal Ordering—Stereochemical Assignment of Plakinic Acids I and J | Zendy

Dalisay Doralyn S. | Zendy; Quach Tim | Zendy; Nicholas Gillian N. | Zendy; Molinski Tadeusz F. | Zendy

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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.

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