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Synthesis and rapid purification of 32 P‐labeled photoactive analogs of farnesyl pyrophosphate
Author(s) -
Turek Tammy C.,
Gaon Igor,
Distefano Mark D.
Publication year - 1997
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199702)39:2<139::aid-jlcr951>3.0.co;2-a
Subject(s) - chemistry , yield (engineering) , benzophenone , specific activity , chromatography , thin layer chromatography , pyrophosphate , chemical synthesis , farnesyl pyrophosphate , alcohol , total synthesis , organic chemistry , biosynthesis , enzyme , biochemistry , in vitro , materials science , metallurgy
To study the binding sites of protein prenyltransferases, we have synthesized photoaffinity labeling analogs that contain photoactive benzophenone units. Here we describe the syntheses and a method for the rapid purification of two 32 P‐labeled analogs; phosphorylation was accomplished by reacting the corresponding alcohols with CCl 3 CN and [ 32 P]‐H 3 PO 4 in CH 3 CN and the purification was performed using C 18 reversed‐phase cartridges. Analog [ 32 P]‐ 3a was prepared from 2.4 mg of starting alcohol 4a and was obtained in 3.3% yield, 50% radiochemical purity and 480 Ci/mol specific activity. Further purification by preparative thin layer chromatography yielded material with a radiochemical purity of 90%. A second analog, [ 32 P]‐ 3b , was prepared from 1.2 mg of alcohol 4b and was obtained in 1.0% yield, 54% radiochemical purity and 700 Ci/mol specific activity. Further purification by preparative thin layer chromatography yielded material with a radiochemical purity of 91%. © 1997 John Wiley & Sons, Ltd.