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Issue 31, 2018
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Synthesis and physicochemical characterization of (6S)-5-formiminotetrahydrofolate; a reference standard for metabolomics

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Abstract

The one-carbon carrier of the formate oxidation level derived from the interaction of tetrahydrofolate and formiminoglutamate, which has been tentatively identified as 5-formiminoltetrahydrofolate, has been prepared by chemical synthesis. Treatment of a solution of (6S)-tetrahydrofolate in aqueous base with excess ethyl formimidate in the presence of anti-oxidant under anaerobic conditions afforded a gummy solid which, based on mass spectral analysis, conformed to a monoformimino derivative of tetrahydrofolate. Further physicochemical characterization by validated methods strongly suggested that the product of chemical synthesis was identical to the enzymatically produced material and that it was, in fact, (6S)-5-formiminotetrahydrofolate. Conditions and handling methods toward maintaining the integrity of this highly sensitive compound were identified and are described, as is analytical methodology, useful for research studies using it.

Graphical abstract: Synthesis and physicochemical characterization of (6S)-5-formiminotetrahydrofolate; a reference standard for metabolomics

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Publication details

The article was received on 29 Jan 2018, accepted on 17 Jul 2018 and first published on 26 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB00245B
Citation: Org. Biomol. Chem., 2018,16, 5684-5690
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    Synthesis and physicochemical characterization of (6S)-5-formiminotetrahydrofolate; a reference standard for metabolomics

    A. H. Lewin, P. Silinski, D. Zhong, A. Gilbert, S. W. Mascarella and H. H. Seltzman, Org. Biomol. Chem., 2018, 16, 5684
    DOI: 10.1039/C8OB00245B

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