Synthesis of tri‐, tetra‐, and penta‐deuterated forms of vitamin a

H. Robert Bergen; Harold C. Furr; James A. Olson

doi:10.1002/jlcr.2580250103

Synthesis of tri‐, tetra‐, and penta‐deuterated forms of vitamin a

H. Robert Bergen, Harold C. Furr, James A. Olson

Biochemistry and Molecular Biology

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

19 Scopus citations

Abstract

The synthesis of 20,20,20‐trideutero, 14,20,20,20‐tetradeutero, 12,14,20,20,20‐pentadeutero, and 10,19,19,19‐tetradeutero analogs of retinoic acid ethyl ester and retinyl acetate, by a modified Wittig‐Horner synthesis, is described. Deuterium was introduced by base‐catalyzed exchange into appropriate intermediates. The 10,19,19,19‐²H₄‐vitamin A, because of its high isotopic integrity (>98% ²H₄), is the preferred analog for biological studies of vitamin A metabolism.

Original language	English (US)
Pages (from-to)	11-21
Number of pages	11
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	25
Issue number	1
DOIs	https://doi.org/10.1002/jlcr.2580250103
State	Published - Jan 1988

Keywords

10,19,19,19‐H‐retinyl acetate
12,14,20,20,20‐H‐retinyl acetate
14,20,20,20‐H‐retinyl acetate
20,20,20‐H‐retinyl acetate
Deuterated vitamin A analogues
deuterated retinyl acetate
retinoid synthesis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

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title = "Synthesis of tri‐, tetra‐, and penta‐deuterated forms of vitamin a",

abstract = "The synthesis of 20,20,20‐trideutero, 14,20,20,20‐tetradeutero, 12,14,20,20,20‐pentadeutero, and 10,19,19,19‐tetradeutero analogs of retinoic acid ethyl ester and retinyl acetate, by a modified Wittig‐Horner synthesis, is described. Deuterium was introduced by base‐catalyzed exchange into appropriate intermediates. The 10,19,19,19‐2H4‐vitamin A, because of its high isotopic integrity (>98% 2H4), is the preferred analog for biological studies of vitamin A metabolism.",

keywords = "10,19,19,19‐H‐retinyl acetate, 12,14,20,20,20‐H‐retinyl acetate, 14,20,20,20‐H‐retinyl acetate, 20,20,20‐H‐retinyl acetate, Deuterated vitamin A analogues, deuterated retinyl acetate, retinoid synthesis",

author = "{Robert Bergen}, H. and Furr, {Harold C.} and Olson, {James A.}",

year = "1988",

month = jan,

doi = "10.1002/jlcr.2580250103",

language = "English (US)",

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T1 - Synthesis of tri‐, tetra‐, and penta‐deuterated forms of vitamin a

AU - Robert Bergen, H.

AU - Furr, Harold C.

AU - Olson, James A.

PY - 1988/1

Y1 - 1988/1

N2 - The synthesis of 20,20,20‐trideutero, 14,20,20,20‐tetradeutero, 12,14,20,20,20‐pentadeutero, and 10,19,19,19‐tetradeutero analogs of retinoic acid ethyl ester and retinyl acetate, by a modified Wittig‐Horner synthesis, is described. Deuterium was introduced by base‐catalyzed exchange into appropriate intermediates. The 10,19,19,19‐2H4‐vitamin A, because of its high isotopic integrity (>98% 2H4), is the preferred analog for biological studies of vitamin A metabolism.

AB - The synthesis of 20,20,20‐trideutero, 14,20,20,20‐tetradeutero, 12,14,20,20,20‐pentadeutero, and 10,19,19,19‐tetradeutero analogs of retinoic acid ethyl ester and retinyl acetate, by a modified Wittig‐Horner synthesis, is described. Deuterium was introduced by base‐catalyzed exchange into appropriate intermediates. The 10,19,19,19‐2H4‐vitamin A, because of its high isotopic integrity (>98% 2H4), is the preferred analog for biological studies of vitamin A metabolism.

KW - 10,19,19,19‐H‐retinyl acetate

KW - 12,14,20,20,20‐H‐retinyl acetate

KW - 14,20,20,20‐H‐retinyl acetate

KW - 20,20,20‐H‐retinyl acetate

KW - Deuterated vitamin A analogues

KW - deuterated retinyl acetate

KW - retinoid synthesis

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Synthesis of tri‐, tetra‐, and penta‐deuterated forms of vitamin a

Abstract

Keywords

ASJC Scopus subject areas

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