Synthesis of Edatrexate (2-13C-glutamate)

Joseph I. DeGraw; William T. Colwell; Thomas Jue

doi:10.1002/(SICI)1099-1344(199702)39:2<99::AID-JLCR949>3.0.CO;2-#

Synthesis of Edatrexate (2-¹³C-glutamate)

Joseph I. DeGraw, William T. Colwell, Thomas Jue

Biochemistry and Molecular Medicine

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

Abstract

The experimental antitumor drug Edatrexate, labeled with 99% ¹³C at the 2-position of the glutamate acid group was required for ¹³C-magnetic resonance spectroscopy studies in biological media. Coupling of 2,4-diamino-4-deoxy-10-ethyl-10-deazapteroic acid with diethyl L-2-¹³C-glutamate as promoted by BOP reagent afforded Edatrexate (2-¹³C-glu) diethyl ester in 60% yield following purification by column chromatography. Saponification by aqueous NaOH in 2-methoxyethanol gave the target molecule in 44% yield or 26% overall.

Original language	English (US)
Pages (from-to)	99-103
Number of pages	5
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	39
Issue number	2
DOIs	https://doi.org/10.1002/(SICI)1099-1344(199702)39:2<99::AID-JLCR949>3.0.CO;2-#
State	Published - Feb 1997

Keywords

C-magnetic resonance spectroscopy
Antitumor
Edatrexate

ASJC Scopus subject areas

Clinical Biochemistry
Molecular Medicine
Analytical Chemistry
Organic Chemistry
Drug Discovery
Pharmacology

Access to Document

10.1002/(SICI)1099-1344(199702)39:2<99::AID-JLCR949>3.0.CO;2-#

Cite this

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title = "Synthesis of Edatrexate (2-13C-glutamate)",

abstract = "The experimental antitumor drug Edatrexate, labeled with 99% 13C at the 2-position of the glutamate acid group was required for 13C-magnetic resonance spectroscopy studies in biological media. Coupling of 2,4-diamino-4-deoxy-10-ethyl-10-deazapteroic acid with diethyl L-2-13C-glutamate as promoted by BOP reagent afforded Edatrexate (2-13C-glu) diethyl ester in 60% yield following purification by column chromatography. Saponification by aqueous NaOH in 2-methoxyethanol gave the target molecule in 44% yield or 26% overall.",

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AU - Jue, Thomas

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