Amplification of the Cotton effect of a single chromophore through liposomal ordering-stereochemical assignment of plakinic acids I and J.
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.
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.
Doralyn S
DS
Dalisay
Tim
T
Quach
Gillian N
GN
Nicholas
Tadeusz F
TF
Molinski
D000085:Acetates / Q000737:chemistry*; D000818:Animals; D002942:Circular Dichroism; D008081:Liposomes / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D047229:Plakortis / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D008081:Liposomes; D010545:Peroxides; C543651:plakinic acid I; C543652:plakinic acid J