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Formylation of tetrahydrofolate by formyl phosphate
Author(s) -
Jahansouz Hossain,
Scherübel Devin M.,
Himes Richard H.
Publication year - 1990
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(90)80231-7
Subject(s) - chemistry , formylation , regioselectivity , reactivity (psychology) , yield (engineering) , medicinal chemistry , phosphate , enzyme , derivative (finance) , catalysis , stereochemistry , organic chemistry , medicine , materials science , alternative medicine , pathology , economics , financial economics , metallurgy
Formyl phosphate is the putative intermediate in the formylation of tetrahydrofolate (THF) catalyzed by N 10 ‐formylTHF synthetase. In this study the non‐enzymic reaction between formyl phosphate and THF was examined at 5°C. 1 H‐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 N 10 ‐form‐ylTHF, N 5 ‐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 O 2 , was also formylated by formyl phosphate, at the oxygen position.