Synthesis and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine

John R. Lever; Karen A. Canella; Clifford L. Eastman; Tomas R. Guilarte

doi:10.1002/jlcr.2580281113

Synthesis and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine

John R. Lever, Karen A. Canella, Clifford L. Eastman, Tomas R. Guilarte

School of Medicine

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

2 Scopus citations

Abstract

The synthesis, purification and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine are described. Bromination of racemic 3‐hydroxykynurenine, catalytic dehalotritiation and purification by ion pair, reverse phase HPLC afforded tritiated material of high radiochemical purity (99.8%) and moderate specific radioactivity (3.64 Ci/mmol). Enantiomerically pure (D)‐ and (L)‐stereoisomers were isolated using chiral HPLC conditions. The stability of the label toward isotopic exchange was assessed to be sufficient for biochemical studies.

Original language	English (US)
Pages (from-to)	1331-1339
Number of pages	9
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	28
Issue number	11
DOIs	https://doi.org/10.1002/jlcr.2580281113
State	Published - Nov 1990

ASJC Scopus subject areas

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

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title = "Synthesis and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine",

abstract = "The synthesis, purification and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine are described. Bromination of racemic 3‐hydroxykynurenine, catalytic dehalotritiation and purification by ion pair, reverse phase HPLC afforded tritiated material of high radiochemical purity (99.8%) and moderate specific radioactivity (3.64 Ci/mmol). Enantiomerically pure (D)‐ and (L)‐stereoisomers were isolated using chiral HPLC conditions. The stability of the label toward isotopic exchange was assessed to be sufficient for biochemical studies.",

author = "Lever, {John R.} and Canella, {Karen A.} and Eastman, {Clifford L.} and Guilarte, {Tomas R.}",

year = "1990",

month = nov,

doi = "10.1002/jlcr.2580281113",

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T1 - Synthesis and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine

AU - Lever, John R.

AU - Canella, Karen A.

AU - Eastman, Clifford L.

AU - Guilarte, Tomas R.

PY - 1990/11

Y1 - 1990/11

N2 - The synthesis, purification and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine are described. Bromination of racemic 3‐hydroxykynurenine, catalytic dehalotritiation and purification by ion pair, reverse phase HPLC afforded tritiated material of high radiochemical purity (99.8%) and moderate specific radioactivity (3.64 Ci/mmol). Enantiomerically pure (D)‐ and (L)‐stereoisomers were isolated using chiral HPLC conditions. The stability of the label toward isotopic exchange was assessed to be sufficient for biochemical studies.

AB - The synthesis, purification and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine are described. Bromination of racemic 3‐hydroxykynurenine, catalytic dehalotritiation and purification by ion pair, reverse phase HPLC afforded tritiated material of high radiochemical purity (99.8%) and moderate specific radioactivity (3.64 Ci/mmol). Enantiomerically pure (D)‐ and (L)‐stereoisomers were isolated using chiral HPLC conditions. The stability of the label toward isotopic exchange was assessed to be sufficient for biochemical studies.

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JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

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ER -

Synthesis and enantiomeric resolution of tritiated (D,L)‐3‐hydroxykynurenine

Abstract

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