Assembly State of Catalytic Modules as Chiral Switches in Asymmetric Strecker Amino Acid Synthesis
Journal of the American Chemical Society2006Vol. 128(21), pp. 6768–6769
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Nobuki Kato, Tsuyoshi Mita, Motomu Kanai, Bruno Therrien, Masaki Kawano, Kentaro Yamaguchi, Hiroshi Danjo, Yoshihisa Sei, Akihiro Sato, Sanae Furusho, Masakatsu Shibasaki
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 alpha,alpha-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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