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Open AccessFeature PaperArticle

Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers

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Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive MC0358, La Jolla, CA 92093, USA
2
Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive MC0358, La Jolla, CA 92093, USA
*
Author to whom correspondence should be addressed.
Present address, Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore.
Mar. Drugs 2017, 15(12), 352; https://doi.org/10.3390/md15120352
Received: 13 October 2016 / Revised: 4 December 2017 / Accepted: 6 December 2017 / Published: 20 December 2017
(This article belongs to the Special Issue Structural Techniques in Natural Products Drug Discovery)
Liposomal circular dichroism (L-CD) of acyclic amino alcohols exhibit amplification of Cotton effects when measured in highly uniform, unilamellar liposomes. The effect is likely due to intermolecular associations—H-aggregates—that self-assemble spontaneously within the lipid bilayer, and persists over long time scales. L-CD spectra of N,O,O′-tri-(6′methoxy-2′-naphthoyl)-d-erythro-sphingosine, or the corresponding dihydro-derivative (sphinganine), shows ~10-fold amplification of magnitudes of Cotton effects over conventional CD spectra recorded in isotropic solution. View Full-Text
Keywords: marine natural product; circular dichroism; exciton coupling; absolute configuration; liposome; sphingosine; sphingolipid marine natural product; circular dichroism; exciton coupling; absolute configuration; liposome; sphingosine; sphingolipid
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MDPI and ACS Style

Molinski, T.F.; Broaddus, C.D.; Morinaka, B.I. Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers. Mar. Drugs 2017, 15, 352.

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