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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of a Tritium Labeled Photolabile Analogue of Farnesyl Diphosphate: (E,e)-[1-3h](2-Diazo-3-Trifluoropropionyloxy)geranyl Diphosphate (Datfp-Gdp)

item Liu, Jinggao - TEXAS A&M UNIVERSITY
item Stipanovic, Robert
item Benedict, C - TEXAS A&M UNIVERSITY

Submitted to: Journal of Labelled Compounds and Radiopharmaceuticals
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 10, 1995
Publication Date: N/A

Interpretive Summary: Cotton produces a group of chemical compounds that equip the plant to defend itself against various pests. The most important of these compounds are all derived from a common intermediate, farnesyl diphosphate (FDP). Purification of the enzyme that convert FDP to these compounds would enhance our ability to manipulate the genes controlling this biosynthesis. A radioactive probe (DATFP-GDP) which attaches itself to the enzyme is known. We have developed an improved synthesis of this probe. This synthesis makes the probe more readily available for studies in cotton and many other plants.

Technical 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) as an aid in isolating enzymes utilizing E,E-FDP as a substrate. We now report an alternative method of synthesizing this probe where in the tritium label is introduced in 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 NaBT4. The DATFP-group successfully withstands both of these oxidation and reduction steps. The overall yield for these two steps was 69%.

Last Modified: 4/22/2015
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