The Structures of the Reoxidation Products of 7,8-Dihydroneopterin

Abstract

Abstract On the reduction of d-erythro-neopterin with sodium dithionite, after which it was let stand in neutral pH, three colorless compounds, I, II, and III, and two yellow compounds, I and II, were obtained. On the reduction of d-erythro-neopterin with Fe dust in 25% acetic acid, after which it was let stand at a neutral pH, two yellow compounds, II and III, were obtained. From UV and NMR spectral data as well as from the chemical reactions, the structures for these compounds were identified, Colorless Compound I is 2-amino-4-hydroxy-6-(1′,3′-dihydroxypropyl)pteridine; Colorless Compound II, 2-amino-4-hydroxy-6-(d-erythro-1′,2′,3′-trihydroxypropyl)-pteridine; Colorless Compound III, 2-amino-4-hydroxy-6-(d-threo1′,2′3′-trihydroxypropyl)pteridine; Yellow Compound I, 2-amino-4-hydroxy-6-(1′-oxo-3′-sulfopropyl)-7,8-dihydropteridine; Yellow Compound II, 2-amino-4-hydroxy-6-(1′-oxo-3′-hydroxypropyl)-7,8-dihydropteridine, and Yellow Compound III, 2-amino-4-hydroxy-6-(1′-oxo-2′,3′-dihydroxypropyl)-7,8-dihydropteridine.