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 - 2009

Fingerprint

Biopterin
Pterins
Glycosides
Glycosylation
Bromides

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Medicine

Cite this

First synthesis of a representative, natural pterin glycoside : 2′-O-(α-D-glucopyranosyl)biopterin. / Hanaya, Tadashi; Yamamoto, Hiroshi; Pfleiderer, Wolfgang.

In: Pteridines, Vol. 20, No. SPECIAL ISSUE, 2009, p. 36-41.

Research output: Contribution to journalArticle

Hanaya, T, Yamamoto, H & Pfleiderer, W 2009, 'First synthesis of a representative, natural pterin glycoside: 2′-O-(α-D-glucopyranosyl)biopterin', Pteridines, vol. 20, no. SPECIAL ISSUE, pp. 36-41.
Hanaya, Tadashi ; Yamamoto, Hiroshi ; Pfleiderer, Wolfgang. / First synthesis of a representative, natural pterin glycoside : 2′-O-(α-D-glucopyranosyl)biopterin. In: Pteridines. 2009 ; Vol. 20, No. SPECIAL ISSUE. pp. 36-41.
@article{e16f3160b46d4efa9dca5317bac14663,
title = "First synthesis of a representative, natural pterin glycoside: 2′-O-(α-D-glucopyranosyl)biopterin",
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.",
keywords = "Biopterin D-glucoside, Glycosylation, Protecting groups, Pterin glycoside",
author = "Tadashi Hanaya and Hiroshi Yamamoto and Wolfgang Pfleiderer",
year = "2009",
language = "English",
volume = "20",
pages = "36--41",
journal = "Pteridines",
issn = "0933-4807",
publisher = "International Society of Pteridinology",
number = "SPECIAL ISSUE",

}

TY - JOUR

T1 - First synthesis of a representative, natural pterin glycoside

T2 - 2′-O-(α-D-glucopyranosyl)biopterin

AU - Hanaya, Tadashi

AU - Yamamoto, Hiroshi

AU - Pfleiderer, Wolfgang

PY - 2009

Y1 - 2009

N2 - 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.

AB - 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.

KW - Biopterin D-glucoside

KW - Glycosylation

KW - Protecting groups

KW - Pterin glycoside

UR - http://www.scopus.com/inward/record.url?scp=77649159684&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77649159684&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:77649159684

VL - 20

SP - 36

EP - 41

JO - Pteridines

JF - Pteridines

SN - 0933-4807

IS - SPECIAL ISSUE

ER -