TY - JOUR
T1 - Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis
AU - Kato, Nobuki
AU - Mita, Tsuyoshi
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
PY - 2006/5/31
Y1 - 2006/5/31
N2 - 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.
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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U2 - 10.1021/ja060841r
DO - 10.1021/ja060841r
M3 - Article
C2 - 16719439
AN - SCOPUS:33744830047
VL - 128
SP - 6768
EP - 6769
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 21
ER -