Synthesis of new deazaflavins with planar chirality. Redox-induced "rope-skipping" racemization

Seiji Shinkai; Toshiro Yamaguchi; Hideki Nakao; Osamu Manabe

doi:10.1016/S0040-4039(00)84327-0

Synthesis of new deazaflavins with planar chirality. Redox-induced "rope-skipping" racemization

Seiji Shinkai, Toshiro Yamaguchi, Hideki Nakao, Osamu Manabe

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

13 Citations (Scopus)

Abstract

New 5-deazaflavins with planar chirality (dFl(n)) were synthesized in which N(3) and O(2′α) in the 10-(2′-hydroxy)phenyl group were linked by a {A figure is presented} chain (n=8,10). (+)-dFl(n=8) showed a large chiral discrimination in fluorescence quenching by (R)- and (S)-1,1′-bi-2- naphthol. (+)-dFl(n=10), which was optically stable at ambient conditions, racemized only when it was converted to the reduced form. This is the first example for redox-induced rope-skipping racemization.

Original language	English
Pages (from-to)	1611-1614
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(00)84327-0
Publication status	Published - Jan 1 1986
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)84327-0

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abstract = "New 5-deazaflavins with planar chirality (dFl(n)) were synthesized in which N(3) and O(2′α) in the 10-(2′-hydroxy)phenyl group were linked by a {A figure is presented} chain (n=8,10). (+)-dFl(n=8) showed a large chiral discrimination in fluorescence quenching by (R)- and (S)-1,1′-bi-2- naphthol. (+)-dFl(n=10), which was optically stable at ambient conditions, racemized only when it was converted to the reduced form. This is the first example for redox-induced rope-skipping racemization.",

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T1 - Synthesis of new deazaflavins with planar chirality. Redox-induced "rope-skipping" racemization

AU - Shinkai, Seiji

AU - Yamaguchi, Toshiro

AU - Nakao, Hideki

AU - Manabe, Osamu

PY - 1986/1/1

Y1 - 1986/1/1

N2 - New 5-deazaflavins with planar chirality (dFl(n)) were synthesized in which N(3) and O(2′α) in the 10-(2′-hydroxy)phenyl group were linked by a {A figure is presented} chain (n=8,10). (+)-dFl(n=8) showed a large chiral discrimination in fluorescence quenching by (R)- and (S)-1,1′-bi-2- naphthol. (+)-dFl(n=10), which was optically stable at ambient conditions, racemized only when it was converted to the reduced form. This is the first example for redox-induced rope-skipping racemization.

AB - New 5-deazaflavins with planar chirality (dFl(n)) were synthesized in which N(3) and O(2′α) in the 10-(2′-hydroxy)phenyl group were linked by a {A figure is presented} chain (n=8,10). (+)-dFl(n=8) showed a large chiral discrimination in fluorescence quenching by (R)- and (S)-1,1′-bi-2- naphthol. (+)-dFl(n=10), which was optically stable at ambient conditions, racemized only when it was converted to the reduced form. This is the first example for redox-induced rope-skipping racemization.

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Synthesis of new deazaflavins with planar chirality. Redox-induced "rope-skipping" racemization

Abstract

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