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Synthesis of a tritium labeled photolabile analogue of farnesyl diphosphate: (E, E)‐[1‐ 3 H]‐(2‐diazo‐3‐trifluoropropionyloxy)geranyl diphosphate (DATFP‐GDP)
Author(s) -
Liu Jinggao,
Stipanovic Robert D.,
Benedict C. R.
Publication year - 1996
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(199602)38:2<139::aid-jlcr817>3.0.co;2-3
Subject(s) - chemistry , geraniol , tritium , yield (engineering) , diazo , aldehyde , alcohol , substrate (aquarium) , organic chemistry , stereochemistry , chromatography , catalysis , physics , nuclear physics , materials science , oceanography , essential oil , metallurgy , geology
Abstract Tritiated (E, E)‐(2‐diazo‐3‐trifluoropropionyloxy)geranyl diphosphate (DATFP‐GDP) has been used as a photolabile analogue of (E, E)‐farnesyl diphosphate (E, E‐FDP) for an aid in isolating enzymes utilizing E, E‐FDP as a substrate. We now report an alternative method of synthesizing this probe in which the tritium label is introduced in the step just before the introduction of the diphosphate group. Thus, DATFP‐geraniol is oxidized to DATFP‐geranial with activated manganese dioxide. The tritium label is introduced by reduction of the aldehyde with NaBT 4 . The DATFP‐group successfully withstands both of these steps. The overall yield for these two steps is 69%. Diphosphorylation of the resulting alcohol afforded DATFP‐[1‐ 3 H]‐GDP in 8% yield with a specific activity of 48.6 μCi/μmol and radiochemical purity of 94%.