Synthesis of a tritium labeled photolabile analogue of farnesyl diphosphate: (E, E)-[1-3H]-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate (DATFP-GDP)
✍ Scribed by Jinggao Liu; Robert D. Stipanovic; C. R. Benedict
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- French
- Weight
- 418 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
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,. The DATFPgroup successfully withstands both of these steps. The overall yield for these two steps is 69%. Diphosphorylation of the resulting alcohol afforded DATFP-[ 1 -3H]-GDP in 8% yield with a specific activity of 48.6 pCi/pmol and radiochemical purity of 94%.