First synthesis of a natural neopterin glycoside: 3'-o-(β-d-glucopyranosyl-uronic acid)neopterin

Tadashi Hanaya, Takafumi Hattori, Daisuke Takayama, Hiroshi Yamamoto

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

1',2'-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]neopterin (1) was prepared from neopterin in 5 steps. Glycosylation of 1 with methyl 2,3,4-tri-O-benzoyl-α-D-glucopyranosyluronate bromide in the presence of silver triflate and tetramethylurea afforded the corresponding 3'-O-(methyl β-D-glucopyranosy-luronate)neopterin derivative (2) in 64% yield. The first synthesis of 3'-O-(β-D- glucopyranosyluronic acid)neopterin was achieved by successive removal (4 steps) of the protecting groups of 2.

Original languageEnglish
Pages (from-to)79-83
Number of pages5
JournalPteridines
Volume21
Issue number3
Publication statusPublished - Sep 2010

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Neopterin
Uronic Acids
Glycosides
Glycosylation
Bromides
Derivatives
Acids

Keywords

  • D-glucronic acid
  • Glycosylation
  • Neopterin glycoside
  • Protecting groups

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Medicine

Cite this

First synthesis of a natural neopterin glycoside : 3'-o-(β-d-glucopyranosyl-uronic acid)neopterin. / Hanaya, Tadashi; Hattori, Takafumi; Takayama, Daisuke; Yamamoto, Hiroshi.

In: Pteridines, Vol. 21, No. 3, 09.2010, p. 79-83.

Research output: Contribution to journalArticle

Hanaya, T, Hattori, T, Takayama, D & Yamamoto, H 2010, 'First synthesis of a natural neopterin glycoside: 3'-o-(β-d-glucopyranosyl-uronic acid)neopterin', Pteridines, vol. 21, no. 3, pp. 79-83.
Hanaya, Tadashi ; Hattori, Takafumi ; Takayama, Daisuke ; Yamamoto, Hiroshi. / First synthesis of a natural neopterin glycoside : 3'-o-(β-d-glucopyranosyl-uronic acid)neopterin. In: Pteridines. 2010 ; Vol. 21, No. 3. pp. 79-83.
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