- Efficient total syntheses of natural neopterin glycosides: Neopterin glucronide and solfapterin
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1,2-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl) ethyl]neopterin (11a) and its 1,2-di-O-benzoyl analog (11b) were prepared from neopterin in 5 steps, respectively. Glycosylation of 11a with methyl 2,3,4-tri-O-benzoylD-glucopyranosyluronate bromide (15b) in the presence of silver triflate afforded the corresponding 3'-O-(β-D-glucopyranosyl) neopterin derivative (18) in 64% yield. The similar treatment of 11b with 2-azido-3,4,6-tri-O-benzoyl-2-deoxy-a-D-glucopyranosyl bromide (21b) provided the corresponding 3'-O-(α-D-glucopyranosyl)neopterin derivative (23a) in 58% yield. The first syntheses of neopterin glucronide (5) and solfapterin (6) were achieved by successive removal of the protecting groups of 18 and 23a, respectively.
- Hanaya, Tadashi,Iwasaki, Katsuya,Saeki, Kaori,Hattori, Takafumi
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p. 390 - 409
(2019/05/21)
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- Synthesis of 5,6,7,8-Tetrahdro-D-neopterine tripolyphosphate. Attempt to Interpret the Biosynthesis of L-Sepiapterine
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The synthesis was achieved by phosphorylation of tetrahydro-5,6,7,8-D-neopterine with polyphosphoric acid.The product is sensitive to light, moisture and oxidation like the other tetrahydropterines.After oxidation in aqueous solution, D,L-sepiapterine was isolated in 5percent yield.The oxidation of non-phosphorilated tetrahydro-5,6,7,8-D-neopterine under the same conditions led to D-sepiapterine without inversion of the configuration.These findings were used to give a tentative explanation for the biosynthesis of natural L-sepiapterine from the D-neopterine.
- Antoulas, Simeon,Viscontini, Max
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p. 1134 - 1139
(2007/10/02)
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