- Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays
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[2H4]Folic acid was synthesized by deuterating p-aminobenzoic acid, which was then coupled to glutamic acid and 6-formylpterin, Using [2H4]folic acid as starting component enabled the preparation of labeled vitamers tetrahydrofolate, 5-formyltetrahydrofolate, 5-methyltetrahydrofolate, and 10-formylfolate which were characterized by electrospray mass spectrometry and collision-induced dissociation. The mass spectrometric studies confirmed that the compounds could be used as internal standards in stable isotope dilution assays.
- Freisleben, Achim,Schieberle, Peter,Rychlik, Michael
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- Preparation of [2',3',5',6'-2H4]pteroylglutamic acid
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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 [2,3,5,6-2H4]benzoyl)-L-glutamic acid diethyl ester was coupled to N(2')-acetyl-6-formylpterin to create [2',3',5',6'-2H4]folic acid. A similar scheme can be used for the preparation of F [1',2',3',4',5',6'-13C6]folic acid from [13C6] ring labeled toluene.
- Dueker,Jones,Smith,Clifford
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p. 981 - 991
(2007/10/02)
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