Journal of Lipid Research, Vol 31, 315-327, Copyright © 1990 by Lipid Research, Inc.
Synthesis and applicability of photolabile 7,7-azo analogues of natural bile salt precursors
T Gengenbacher, W Gerok, U Giese and G Kurz
Institut fur Organische Chemie and Biochemie, Universitat Freiburg, F.R.G.
In an approach to the identification of proteins involved in the side chain
degradation of bile salt biosynthesis, the photolabile 7,7-azo derivatives
of 5 beta-cholestane-3 alpha,7 alpha,12 alpha-triol, 5 beta- cholestane-3
alpha,7 alpha,12 alpha,26-tetrol and 3 alpha,7 alpha,12 alpha-trihydroxy-5
beta-cholestan-26-oate were synthesized. All 7,7-azo derivatives were
metabolized by intact rat liver and freshly isolated rat hepatocytes in the
same manner as the nonphotolabile physiological intermediates, resulting in
the formation of the 7,7-azo analogues of cholyltaurine and cholylglycine.
Photolysis of all three photolabile derivatives, using a light source with
a maximum emission at 350 nm, occurred with a half-life of 2.1 min; their
efficacy for photoaffinity labeling was demonstrated by incorporation into
rat serum albumin.
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