73573-51-0Relevant academic research and scientific papers
Studies on Biologically Active Pteridines. VII. Absolute Configuration of (-)-6-Methyltetrahydropterin Produced by Enzymic Reduction
Matsuura, Sadao,Sugimoto, Takashi
, p. 2543 - 2544 (2007/10/02)
The C-6 configuration of (-)-6-methyltetrahydropterin, produced by enzymic reduction of the 7,8-dihydro precursor, is shown to be S by a synthesis.Condensation of 2,4-diamino-5-bromo-6-hydroxypyrimidine with (S)-1,2-propanediamine gave (S)-6-methyltetrahydropterin.Examination of CD spectra of the 6-methyltetrahydropterins from the two origins led to the above conclusion.
Absolute Configuration of 6-Methyl-5,6,7,8-tetrahydropterin produced by Enzymic Reduction (Dihydrofolate Reductase and NADPH) of 6-Methyl-7,8-dihydropterin
Armarego, Wilfred L. F.,Waring, Paul,Williams, Jeffrey W.
, p. 334 - 336 (2007/10/02)
Dihydrofolate reductase (5,6,7,8-tetrahydrofolate: NADP oxidoreductase, E.C.1.5.1.3.) and NADPH, which catalyse the reduction of 7,8-dihydrofolic acid (1) stereospecifically to give one diastereoisomer of 5,6,7,8-tetrahydrofolic acid (3), also catalyse the reduction of 6-methyl-7,8-dihydropterin (2) stereospecifically to (-)-6-methyl-5,6,7,8-tetrahydropterin (4); the absolute configuration at C-6 of the pterin (4) is shown to be S by correlation with S-alanine using a series of methylations, degradations, and syntheses, and if the most probable assumption is made that the stereospecificities of these two reactions are the same, then the absolute configuration at C-6 of enzymically produced 5,6,7,8-tetrahydrofolic acid should be S.
