Synthesis and optical resolution of a new flavin with axial chirality and redox-dependent racemization

Seiji Shinkai, Hideki Nakao, Osamu Manabe

研究成果: ジャーナルへの寄稿記事

8 引用 (Scopus)

抄録

A new flavin (3-methyl-10-(2′-phenyl)phenylisoalloxazine) with restricted rotation about the C(1′)-N(10) single bond was synthesized and optically resoluted for the first time. (+)- Isomer (100% enantiomeric purity) did not racemize at ambient conditions, whereas it racemized invariably when it was reduced (by four different methods). The kinetic studies proved that the novel racemization mode is attributed to conversion of the "planar" oxidized form to the "bent" reduced form.

元の言語英語
ページ(範囲)5183-5186
ページ数4
ジャーナルTetrahedron Letters
26
発行部数42
DOI
出版物ステータス出版済み - 1 1 1985
外部発表Yes

Fingerprint

Chirality
Isomers
Oxidation-Reduction
Kinetics
4,6-dinitro-o-cresol
single bond

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

これを引用

Synthesis and optical resolution of a new flavin with axial chirality and redox-dependent racemization. / Shinkai, Seiji; Nakao, Hideki; Manabe, Osamu.

:: Tetrahedron Letters, 巻 26, 番号 42, 01.01.1985, p. 5183-5186.

研究成果: ジャーナルへの寄稿記事

Shinkai, Seiji ; Nakao, Hideki ; Manabe, Osamu. / Synthesis and optical resolution of a new flavin with axial chirality and redox-dependent racemization. :: Tetrahedron Letters. 1985 ; 巻 26, 番号 42. pp. 5183-5186.
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