Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin

Abstract

the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.

A regioselective synthesis of the dephospho ditholene protected molybdopterin

“…The 1 H NMR spectra of 9 are shown in Figure 1. Consistent with the literature 11, 40 a peak at 8.97 ppm corresponding to one proton is assigned to the proton at C7 in the pterin ring. Resonances due to the NH and NH 2 groups appear at 11.87 and 7.31 ppm, respectively, and the signals disappear in the presence of D 2 O.…”

Pterin chemistry and its relationship to the molybdenum cofactor

“…The major isomer in the case of biopterin is an L-isomer while that in neopterin is a D-isomer. In some cases, one of the hydroxy groups is glycosylated to give different derivatives of naturally occurring biopterin and neopterin [18]. The fully reduced form, tetrahydrobiopterin (H4biopterin) was first recognized as the redox cofactor for the aromatic amino acid hydroxylases such as phenylalanine hydroxylase (PAH).…”

Synthesis of biopterin and related pterin glycosides

“…Indeed methanolysis of 29 and subsequent acetalization and p ‐methoxybenzylation afforded the 2,3‐di‐ O ‐PMB derivative ( 30 ). Hydrolysis of 30 , followed by acetylation, provided the 4,6‐di‐ O ‐acetyl derivative ( 31 ), which was converted into the glycosyl bromide ( 32 ) by the action of bromine (41).…”

“…The α‐anomeric structure of 34a was deduced from its J 1,2 value (3.9 Hz) in the proton‐nuclear magnetic resonance ( 1 H NMR) spectra, while the larger J 1,2 value (8.1 Hz) confirmed the β‐form of 34b . Removal of the protecting groups of 34a by the usual procedures has led to the first synthesis of 2′‐ O ‐(α‐ D ‐glucopyranosyl)biopterin ( 1b ) (41).…”