Pterins. VIII. The absolute configuration at C 6 of natural 2-Amino-6-[(1'R,2'S)- 1',2'-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(3H)-one (L-erythro-5,6,7,8-tetrahydrobiopterin)

Abstract

The conformation of the side chain of 5,6,7,8-tetrahydrobiopterint (6) in 0.5 M DCl/D₂O is predominantly quasi-equatorial (deduced from ³J (¹³C4a, ¹H6) 1.1 HZ), and is the same as that of the methyl group in 2-methyl-1,2,3,4-tetrahydroquinoxaline and in 2-amino-6-methyl-5,6,7,8-tetrahydropteridin-4(3H)-one in the same solvent. Because (-)-(2S)-2-methyl-1,2,3,4-tetrahydroquinoxaline(4) and (-)-(6S)-2-amino-6-methyl-5,6,7,8-tetrahydropteridin-4(3H)-one (5) have the same conformation and negative c.d. spectra (O 248 nm and 263 nm respectively) as does the natural 5,6,7,8, tetrahydrobiopterin (O minimum at 265 nm) in 0.1 M hydrochloric acid, then the absolute conformations of the tetrahydropyrazine rings and the absolute configurations at the chiral centres C2, C6, and C6 of compounds (4), (5) and (6) respectively are the same. Hence the absolute configuration at C6 in natural 5,6,7,8 tetrahydrobiopterin is R. 

A convenient synthesis of biopterin on a gram scale is described.