HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Stoll, G. H. Articles by Kurz, G. Search for Related Content PubMed PubMed Citation Articles by Stoll, G. H. Articles by Kurz, G. Social Bookmarking                      What's this?

Journal of Lipid Research, Vol 32, 843-857, Copyright © 1991 by Lipid Research, Inc.

ARTICLES

Synthesis of a metabolically stable modified long-chain fatty acid salt and its photolabile derivative

GH Stoll, R Voges, W Gerok and G Kurz
Institut fur Organische Chemie and Biochemie, Universitat Freiburg, Germany.

An analogue of the long-chain fatty acid salt, sodium stearate, was synthesized in which the hydrogen atoms at carbons 2, 3, and 18 were replaced by fluorine. The key step in the synthesis was the addition of 3-iodo-2,2,3,3-tetrafluoropropanoic acid amide to 15,15,15-trifluoro-1- pentadecene. Radioactivity was introduced by catalytic reduction of 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid amide with carrier- free tritium gas yielding a product with the specific radioactivity of 2.63 TBq/mmol. The resulting 2,2,3,3,18,18,18-heptafluoro-4- octadecenoic acid has a pKa of about 0.5 and is completely dissociated under normal physiological conditions. The fluorinated fatty acid salt analogue is readily taken up into hepatocytes and proved to be metabolically inert. In an approach to the identification of proteins involved in long-chain fatty acid salt transport across membranes and intracellular compartments, the photolabile derivative 11,11-azo- 2,2,3,3,18,18,18-heptafluoro[G-3H]octadecanoic acid sodium salt was synthesized with a specific radioactivity of 2.63 TBq/mmol. Photolysis of the photolabile derivative, using a light source with a maximum emission at 350 nm, occurred with a half-life of 1.5 min. The generated carbene reacted with 14C-labeled methanol and acetonitrile with covalent bond formation of 6-13%. Its efficacy for photoaffinity labeling was demonstrated by incorporation into serum albumin, the extracellular fatty acid salt-binding protein, as well as into the intracellular fatty acid salt-binding protein (FABP) of rat liver with the molecular weight of 14,000.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				D. D. Stump, X. Fan, and P. D. Berk Oleic acid uptake and binding by rat adipocytes define dual pathways for cellular fatty acid uptake J. Lipid Res., April 1, 2001; 42(4): 509 - 520. [Abstract] [Full Text]

				W. Schmider, A. Fahr, H. E. Blum, and G. Kurz Transport of heptafluorostearate across model membranes. Membrane transport of long-chain fatty acid anions I J. Lipid Res., May 1, 2000; 41(5): 775 - 787. [Abstract] [Full Text]