First synthesis of a representative, natural pterin glycoside: 2′-O-(α-D-glucopyranosyl)biopterin

Tadashi Hanaya, Hiroshi Yamamoto, Wolfgang Pfleiderer

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Glycosylation of N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (14) with the novel donor 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-D-glucopyranosyl bromide (19) in the presence of silver triflate and tetramethylurea predominantly afforded the corresponding α-D-glucopyranoside (20a), from which 2′-O-(α-D-glucopyranosyl)biopterin (1) was obtained by the successive removal of the protecting groups.

Original languageEnglish
Pages (from-to)36-41
Number of pages6
JournalPteridines
Volume20
Issue numberSPECIAL ISSUE
Publication statusPublished - Dec 1 2009

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Clinical Biochemistry

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