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Journal of Lipid Research, Vol 24, 910-923, Copyright © 1983 by Lipid Research, Inc.
W Kramer and G Kurz
In an approach to the identification of bile salt-binding carriers, the
photoactivable bile acid derivatives A) 3 beta-azido, 7 alpha,12 alpha-
dihydroxy-5 beta-cholan-24-oic acid, B) 7,7-azo-3 alpha,12 alpha-
dihydroxy-5 beta-cholan-24-oic acid, and C) 11 xi-azido-12-oxo-3 alpha,7
alpha-dihydroxy-5 beta-cholan-24-oic acid were synthesized in unconjugated
and taurine-conjugated form. Photolysis of the 3 beta- azido derivatives
was studied using a light source with a maximum emission at 300 nm and
established a half-life time of 18.5 min. The photochemistry of the 7,7-azo
derivatives was investigated using light with a maximum at 350 nm and had a
half-life time of 2.2 min. The 11 xi- azido-12-oxo derivatives were
photolyzed with light having a maximum at 300 nm resulting in a half-life
time of 8.5 min. The suitability of the 7,7-azo derivatives for
photoaffinity labeling was demonstrated by photolyses in 14C-labeled
methanol and acetonitrile. The generated carbene reacted with the solvents
under covalent bond formation of 6 to 12%. The efficiency of all
synthesized photolabile derivatives for photoaffinity labeling of bile salt
binding proteins was demonstrated.
ARTICLES
Photolabile derivatives of bile salts. Synthesis and suitability for photoaffinity labeling
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