title: Assembly state of catalytic modules as chiral switches in asymmetric Strecker amino acid synthesis.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Nobuki
authors.initials: N
authors.lastname: Kato
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Mita
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
authors.forename: Bruno
authors.initials: B
authors.lastname: Therrien
authors.forename: Masaki
authors.initials: M
authors.lastname: Kawano
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Danjo
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Sei
authors.forename: Akihiro
authors.initials: A
authors.lastname: Sato
authors.forename: Sanae
authors.initials: S
authors.lastname: Furusho
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003460:Crystallization; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D000596:Amino Acids