First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae

Tadashi Hanaya; Hiroshi Yamamoto

doi:10.1515/pterid-2013-0005

First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae

Tadashi Hanaya, Hiroshi Yamamoto

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

2 Citations (Scopus)

Abstract

The key precursor, N²-(N,N-dimethylaminomethylene)-6- hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl) ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3 H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri- O-benzoyl-β-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding β-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).

Original language	English
Pages (from-to)	3-6
Number of pages	4
Journal	Pteridines
Volume	24
Issue number	1
DOIs	https://doi.org/10.1515/pterid-2013-0005
Publication status	Published - Jun 2013

Keywords

Asperopterin
Glycosylation
Isoxanthopterin
Protecting groups
Pterin glycoside

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Clinical Biochemistry

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title = "First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae",

abstract = "The key precursor, N2-(N,N-dimethylaminomethylene)-6- hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl) ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3 H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri- O-benzoyl-β-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding β-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).",

keywords = "Asperopterin, Glycosylation, Isoxanthopterin, Protecting groups, Pterin glycoside",

author = "Tadashi Hanaya and Hiroshi Yamamoto",

year = "2013",

month = jun,

doi = "10.1515/pterid-2013-0005",

language = "English",

volume = "24",

pages = "3--6",

journal = "Pteridines",

issn = "0933-4807",

publisher = "International Society of Pteridinology",

number = "1",

}

TY - JOUR

T1 - First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae

AU - Hanaya, Tadashi

AU - Yamamoto, Hiroshi

PY - 2013/6

Y1 - 2013/6

N2 - The key precursor, N2-(N,N-dimethylaminomethylene)-6- hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl) ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3 H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri- O-benzoyl-β-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding β-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).

AB - The key precursor, N2-(N,N-dimethylaminomethylene)-6- hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl) ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3 H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri- O-benzoyl-β-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding β-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).

KW - Asperopterin

KW - Glycosylation

KW - Isoxanthopterin

KW - Protecting groups

KW - Pterin glycoside

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DO - 10.1515/pterid-2013-0005

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SN - 0933-4807

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JO - Pteridines

JF - Pteridines

IS - 1

ER -

First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae

Abstract

Keywords

ASJC Scopus subject areas

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