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 |
| 巻 | 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 |
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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
}
TY - JOUR
T1 - Synthesis and optical resolution of a new flavin with axial chirality and redox-dependent racemization
AU - Shinkai, Seiji
AU - Nakao, Hideki
AU - Manabe, Osamu
PY - 1985/1/1
Y1 - 1985/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=46549103212&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=46549103212&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)98898-1
DO - 10.1016/S0040-4039(00)98898-1
M3 - Article
AN - SCOPUS:46549103212
VL - 26
SP - 5183
EP - 5186
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 42
ER -