An abbreviated synthesis of tetrahydropteridines.
5,6,7,8-Tetrahydrobiopterin, the naturally occurring essential cofactor for the enzymatic hydroxylations of phenylalanine, tyrosine and tryptophan, and its synthetic analog 2-amino-6-methyl-5,6,7,8-tetrahydro-4(3H)-pteridinone, have been synthesized in good yield by the direct hydrogenation of 1-(2-amino-1,6-dihydro-5-nitro-6-oxopyrimidin-4-yl-amino)-1,5-dide oxy-L- erythro-pentulose and 2-amino-6-hydroxy-5-phenylazo-4-pyrimidylamino-acetone, respectively. The reactions were carried out at room temperature in trifluoroacetic acid over a platinum catalyst at 2 atm and the products, each containing a mixture of the two possible C-6 isomers, were isolated by precipitation. The simplicity of the preparative method suggests the procedure may be applied generally to the synthesis of all tetrahydropteridines derived from similar pyrimidine precursors.
D001708:Biopterins / Q000031:analogs & derivatives / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D007536:Isomerism; D011621:Pteridines / Q000138:chemical synthesis*; D011622:Pterins / Q000138:chemical synthesis; D013696:Temperature
D011621:Pteridines; D011622:Pterins; D001708:Biopterins; C017523:6-methyltetrahydropterin; C003402:sapropterin