An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin

Tadashi Hanaya, Kiyoshi Torigoe, Kazuyuki Soranaka, Hirofumi Fujita, Hiroshi Yamamoto, Wolfgang Pfleiderer

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

Original languageEnglish
Pages (from-to)72-78
Number of pages7
JournalPteridines
Volume19
Issue number3
Publication statusPublished - Sep 2008

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Biopterin
Glycosylation
Derivatives

Keywords

  • Biopterin D-riboside
  • Glycosylation
  • Protecting groups
  • Pterin glycoside

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Medicine

Cite this

Hanaya, T., Torigoe, K., Soranaka, K., Fujita, H., Yamamoto, H., & Pfleiderer, W. (2008). An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin. Pteridines, 19(3), 72-78.

An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin. / Hanaya, Tadashi; Torigoe, Kiyoshi; Soranaka, Kazuyuki; Fujita, Hirofumi; Yamamoto, Hiroshi; Pfleiderer, Wolfgang.

In: Pteridines, Vol. 19, No. 3, 09.2008, p. 72-78.

Research output: Contribution to journalArticle

Hanaya, T, Torigoe, K, Soranaka, K, Fujita, H, Yamamoto, H & Pfleiderer, W 2008, 'An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin', Pteridines, vol. 19, no. 3, pp. 72-78.
Hanaya T, Torigoe K, Soranaka K, Fujita H, Yamamoto H, Pfleiderer W. An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin. Pteridines. 2008 Sep;19(3):72-78.
Hanaya, Tadashi ; Torigoe, Kiyoshi ; Soranaka, Kazuyuki ; Fujita, Hirofumi ; Yamamoto, Hiroshi ; Pfleiderer, Wolfgang. / An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin. In: Pteridines. 2008 ; Vol. 19, No. 3. pp. 72-78.
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AU - Pfleiderer, Wolfgang

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N2 - N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

AB - N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

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