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

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

11 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ（範囲）918-927
ページ数10
ジャーナルHelvetica Chimica Acta
巻84
号4
DOI
出版ステータス出版済み - 2001
外部発表はい

All Science Journal Classification (ASJC) codes

  • 触媒
  • 生化学
  • 創薬
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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