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

Tadashi Hanaya; Hiroshi Yamamoto; Wolfgang Pfleiderer

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

Tadashi Hanaya, Hiroshi Yamamoto, Wolfgang Pfleiderer

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	36-41
Number of pages	6
Journal	Pteridines
Volume	20
Issue number	SPECIAL ISSUE
Publication status	Published - 2009

Keywords

Biopterin D-glucoside
Glycosylation
Protecting groups
Pterin glycoside

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Clinical Biochemistry

Cite this

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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.",

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author = "Tadashi Hanaya and Hiroshi Yamamoto and Wolfgang Pfleiderer",

year = "2009",

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volume = "20",

pages = "36--41",

journal = "Pteridines",

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publisher = "International Society of Pteridinology",

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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

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M3 - Article

AN - SCOPUS:77649159684

SN - 0933-4807

VL - 20

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EP - 41

JO - Pteridines

JF - Pteridines

IS - SPECIAL ISSUE

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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