Long-Range Stereo-Relay:  Relative and Absolute Configuration of 1,n-Glycols from Circular Dichroism of Liposomal Porphyrin Esters

John B. MacMillan and Tadeusz F. Molinski*
Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616
J. Am. Chem. Soc., 2004, 126 (32), pp 9944–9945
DOI: 10.1021/ja047741a
Publication Date (Web): July 24, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, tfmolinski@ucdavis.edu

Abstract

Abstract Image

The relative and absolute configurations of long-chain syn- and anti-1,5-, 1,7- and 1,9-glycols were determined from exciton-coupled circular dichroism (ECCD) of the corresponding bis-5-(4‘-carboxyl)-5,10,15,20-tetraphenylporphyrin esters measured in uniform (phi = 26 nm), unilamellar liposomes. Long-range transmission of configuration by ECCD is made possible through partial ordering of glycol ester−lipid molecules by liposomal bilayers.

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History

  • Published In Issue August 18, 2004
  • Received April 19, 2004

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