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

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

doi:10.1016/0045-2068(86)90017-9

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

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

Research output: Contribution to journal › Article › peer-review

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 ³H¹⁴C ratios. The methods described should prove advantageous over existing procedures for radiochemical preparations of this class of metabolites.

Original language	English (US)
Pages (from-to)	46-54
Number of pages	9
Journal	Bioorganic Chemistry
Volume	14
Issue number	1
DOIs	https://doi.org/10.1016/0045-2068(86)90017-9
State	Published - Mar 1986
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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@article{a957c24cfc7a4fd8ab8987901a0f7ec6,

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

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.",

author = "{Jo Davisson}, V. and {Mark Zabriskie}, T. and Poulter, {C. Dale}",

note = "Funding Information: i This research was supported by Research Grants GM-21328 and GM-25521 from the National Institutes of Health. 2 Author to whom correspondence should",

year = "1986",

month = mar,

doi = "10.1016/0045-2068(86)90017-9",

language = "English (US)",

volume = "14",

pages = "46--54",

journal = "Bioorganic Chemistry",

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publisher = "Academic Press Inc.",

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T1 - Radiolabeled allylic isoprenoid pyrophosphates

T2 - Synthesis, purification, and determination of specific activity

AU - Jo Davisson, V.

AU - Mark Zabriskie, T.

AU - Poulter, C. Dale

N1 - Funding Information: i This research was supported by Research Grants GM-21328 and GM-25521 from the National Institutes of Health. 2 Author to whom correspondence should

PY - 1986/3

Y1 - 1986/3

N2 - 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.

AB - 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.

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SP - 46

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JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

IS - 1

ER -

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

Abstract

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