Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis

Takashi Sugimoto, Kazuhisa Ikemoto, Shizuaki Murata, Masahiro Tazawa, Takahide Nomura, Yasumichi Hagino, Hiroshi Ichinose, Toshiharu Nagatsu

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10 Citations (Scopus)

Abstract

The structure of the native pteridine in Tetrahymena pyriformis was determined as (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3-trihydroxypropyl] pteridin-4(3H)-one; 4). First, the configuration of the 1,2,3-trihydroxypropyl side chain was confirmed as D-threo by the fluorescence-detected circular dichroism (FDCD) spectrum of its aromatic pterin derivative 2 obtained by I2 oxidation (Fig. 1). The configuration at the 6-position of 4 was determined as (R) by comparison of its hexaacetyl derivative 6 with authentic (6R)- and (6S)-hexaacetyl-5,6,7,8-tetrahydro-D-monapterins 6 and 7, respectively, in the HPLC, LC/MS, and LC-MS/MS (Figs. 3-6). (6R)-5,6,7,8-Tetrahydro-D-monapterin (4) is a newly discovered natural tetrahydropterin.

Original languageEnglish
Pages (from-to)918-927
Number of pages10
JournalHelvetica Chimica Acta
Volume84
Issue number4
DOIs
Publication statusPublished - 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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