Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis

Nobuki Kato; Tsuyoshi Mita; Motomu Kanai; Bruno Therrien; Masaki Kawano; Kentaro Yamaguchi; Hiroshi Danjo; Yoshihisa Sei; Akihiro Sato; Sanae Furusho; Masakatsu Shibasaki

doi:10.1021/ja060841r

Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis

Nobuki Kato, Tsuyoshi Mita, Motomu Kanai, Bruno Therrien, Masaki Kawano, Kentaro Yamaguchi, Hiroshi Danjo, Yoshihisa Sei, Akihiro Sato, Sanae Furusho, Masakatsu Shibasaki

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

110 Citations (Scopus)

Abstract

Self-assembled chiral polymetallic complexes often demonstrate novel properties as asymmetric catalysts. We report the three-dimensional structures of two such asymmetric catalysts (crystals A and B) for Strecker α,α-disubstituted amino acid synthesis. These complexes are constructed via assembly of the same chiral modules derived from d-glucose, but their assembly modes differ. The enantioselectivity in the Strecker reaction was dramatically switched, depending on which assembly mode was used: the catalyst generated in situ whose structure is represented by crystal B, or by crystal A. These findings provide insight into the functional importance of higher-order structures of an artificial catalyst.

Original language	English
Pages (from-to)	6768-6769
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	21
DOIs	https://doi.org/10.1021/ja060841r
Publication status	Published - 2006 May 31
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja060841r

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Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis. / Kato, Nobuki; Mita, Tsuyoshi; Kanai, Motomu; Therrien, Bruno; Kawano, Masaki; Yamaguchi, Kentaro; Danjo, Hiroshi; Sei, Yoshihisa; Sato, Akihiro; Furusho, Sanae; Shibasaki, Masakatsu.

In: Journal of the American Chemical Society, Vol. 128, No. 21, 31.05.2006, p. 6768-6769.

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

Kato, Nobuki ; Mita, Tsuyoshi ; Kanai, Motomu ; Therrien, Bruno ; Kawano, Masaki ; Yamaguchi, Kentaro ; Danjo, Hiroshi ; Sei, Yoshihisa ; Sato, Akihiro ; Furusho, Sanae ; Shibasaki, Masakatsu. / Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 21. pp. 6768-6769.

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AU - Kato, Nobuki

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AU - Kanai, Motomu

AU - Therrien, Bruno

AU - Kawano, Masaki

AU - Yamaguchi, Kentaro

AU - Danjo, Hiroshi

AU - Sei, Yoshihisa

AU - Sato, Akihiro

AU - Furusho, Sanae

AU - Shibasaki, Masakatsu

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AB - Self-assembled chiral polymetallic complexes often demonstrate novel properties as asymmetric catalysts. We report the three-dimensional structures of two such asymmetric catalysts (crystals A and B) for Strecker α,α-disubstituted amino acid synthesis. These complexes are constructed via assembly of the same chiral modules derived from d-glucose, but their assembly modes differ. The enantioselectivity in the Strecker reaction was dramatically switched, depending on which assembly mode was used: the catalyst generated in situ whose structure is represented by crystal B, or by crystal A. These findings provide insight into the functional importance of higher-order structures of an artificial catalyst.

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Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis

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ASJC Scopus subject areas

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