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

Seiji Shinkai; Hideki Nakao; Osamu Manabe

doi:10.1016/S0040-4039(00)98898-1

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

Seiji Shinkai, Hideki Nakao, Osamu Manabe

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	5183-5186
Number of pages	4
Journal	Tetrahedron Letters
Volume	26
Issue number	42
DOIs	https://doi.org/10.1016/S0040-4039(00)98898-1
Publication status	Published - Jan 1 1985
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)98898-1

Cite this

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abstract = "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.",

author = "Seiji Shinkai and Hideki Nakao and Osamu Manabe",

year = "1985",

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doi = "10.1016/S0040-4039(00)98898-1",

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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.

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SP - 5183

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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