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

Tadashi Hanaya, Hiroshi Yamamoto

Research output: Contribution to journalArticle

1 Citation (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 languageEnglish
Pages (from-to)3-6
Number of pages4
JournalPteridines
Volume24
Issue number1
DOIs
Publication statusPublished - Jun 2013

Fingerprint

Xanthopterin
Pteridines
Aspergillus oryzae
Glycosylation
Tin
Aspergillus
Glycosides
Chlorides
1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose
4-nitrophenyl
isoxanthopterin
stannous chloride

Keywords

  • Asperopterin
  • Glycosylation
  • Isoxanthopterin
  • Protecting groups
  • Pterin glycoside

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Medicine

Cite this

First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae. / Hanaya, Tadashi; Yamamoto, Hiroshi.

In: Pteridines, Vol. 24, No. 1, 06.2013, p. 3-6.

Research output: Contribution to journalArticle

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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).

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