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Preparation of [2′,3′,5′,6′-2H4]pteroylglutamic acid

✍ Scribed by Stephen R. Dueker; A. Daniel Jones; Gary M. Smith; Andrew J. Clifford

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
444 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Folic acid plays a key role in nucleic acid biosynthesis, essential for normal cell proliferation and function. Localized folate deficiencies may be related to changes in cytology associated with cancer development; analogs of folic acid, such as methotrexate, are potent chemotherapeutic agents and are widely used either alone or in combination therapy for many types of cancer. In this report we describe the synthesis of a tetra‐deuterated folic acid from perdeuterated toluene. The primary intermediate, N‐(4‐amino [2,3,5,6‐^2^H~4~]benzoyl)‐L‐glutamic acid diethyl ester was coupled to N(2′)‐acetyl‐6‐formylpterin to create [2′,3′,5′,6′‐^2^H~4~]folic acid. A similar scheme can be used for the preparation of [1′,2′,3′,4′,5′,6′‐^13^C~6~]folic acid from [^13^C~6~] ring labeled toluene.

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