Formylation of tetrahydrofolate by formyl phosphate

FEBS Letters

Scherübel, Devin M.¹  Jahansouz, Hossain¹  Himes, Richard H.¹ 

[1] Department of Biochemistry, University of Kansas, Lawrence, KS 66045-2106, USA

关键词: Formyl phosphate;    Tetrahydrofolate;    Formyltetrahydrofolate synthetase;    N10;   

DOI  :  10.1016/0014-5793(90)80231-7

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

Formyl phosphate is the putative intermediate in the formylation of tetrahydrofolate (THF) catalyzed by N¹⁰-formylTHF synthetase. In this study the non-enzymic reaction between formyl phosphate and THF was examined at 5°C. ¹H-NMR, HPLC and kinetic analysis of the proton-catalyzed conversion of the product to N^5,10-methenylTHF were used to identify the product. In contrast to the enzyme reaction, which produces N¹⁰-form-ylTHF, N⁵-formylTHF was the only formylated THF derivative formed. The reaction was conducted at pH values of 3, 5, and 7, with the highest yield being obtained at pH 5 (64–85%, based on THF). The enzyme, therefore, changes the regioselectivity of this reaction by increasing the reactivity of the 10-nitrogen and either decreasing the reactivity of the 5-nitrogen or limiting its accessibility to formyl phosphate. 2-Mercaptoethanol, present in the reaction mixture to protect THF from O₂, was also formylated by formyl phosphate, at the oxygen position.

【 授权许可】

Unknown