Radiolabeled allylic isoprenoid pyrophosphates: Synthesis, purification, and determination of specific activity

V. Jo Davisson, T. Mark Zabriskie, C. Dale Poulter

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

A new procedure for the preparation of [1-3H]allylic isoprenoid pyrophosphates is reported. Tritium is introduced into dimethylallyl alcohol, geraniol, and farnesol by oxidation to the corresponding aldehydes followed by reduction with sodium [1-3H]borohydride. The alcohols are phosphorylated by conversion to allylic halides and treatment of the halides with tris-tetra-n-butylammonium hydrogen pyrophosphate. The pyrophosphates are purified by chromatography on cellulose. Specific activities are determined from the corresponding naphthoate esters whose concentrations can be measured accurately by ultraviolet spectroscopy. Alternatively, the specific activity of tritium is determined for the naphthoate esters prepared with [14C]naphthoic acid of known specific activity by measurement of 3H 14C ratios. The methods described should prove advantageous over existing procedures for radiochemical preparations of this class of metabolites.

Original languageEnglish (US)
Pages (from-to)46-54
Number of pages9
JournalBioorganic Chemistry
Volume14
Issue number1
DOIs
StatePublished - Mar 1986

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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