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Carbocyclic glycinamide ribonucleotide is a substrate for glycinamide ribonucleotide transformylase
Authors:C A Caperelli  M F Price
Institution:Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, Pennsylvania 19111.
Abstract:The carbocyclic analog of glycinamide ribonucleotide has been synthesized from the racemic parent trihydroxy cyclopentyl amine (B.L. Kam and N.J. Oppenheimer (1981) J. Org. Chem. 46, 3268-3272). This analog was accepted as a substrate (Km = 18 microM, Vmax = 0.23 mM/min) by mammalian glycinamide ribonucleotide transformylase (EC 2.1.2.2) with an efficiency comparable to that of the natural substrate glycinamide ribonucleotide (Km = 10 microM, Vmax = 0.27 mM/min). For each molecule of 10-formyl-5,8-dideazafolate cosubstrate consumed, 0.92 molecule of N-formyl carbocyclic glycinamide ribonucleotide was produced in the enzymatic reaction, indicating a 1:1 stoichiometry. These studies afford the first alternate nucleotide substrate for glycinamide ribonucleotide transformylase and suggest that the ribose ring oxygen of glycinamide ribonucleotide is not critical for enzyme recognition and binding.
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