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Chiral Recognition by Functionalized Cyclodextrin Metal Complexes

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Transition Metals in Supramolecular Chemistry

Part of the book series: NATO ASI Series ((ASIC,volume 448))

Abstract

The copper(II) complexes of β-cyclodextrins functionalized with aliphatic or pseudoaromatic amines were used for the chiral recognition of unmodified amino acids. Molecular recognition, assisted by non-covalent interactions, was proved by means of thermodynamic and spectroscopic (c.d., e.p.r. and fluorescence) measurements. A cis-disposition of amino groups seems to assist enantiomeric selectivity. The copper(II)-β-cyclodextrin complexes can be used as mobile phase additives in HPLC to separate enantiomeric mixtures of unmodified aromatic amino acids.

Chiral discrimination seems to occur mainly in the aqueous phase and enantioselectivity may be directly related to different complex stabilities in the aqueous phase.

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Authors and Affiliations

  1. Dipartimento Scienze Chimiche, Università di Catania, Italy

    G. Maccarrone & E. Rizzarelli

  2. Istituto per lo Studio delle Sostanze Naturali di Interesse Alimentare e Chimico-Farmaceutico del C.N.R., v.le A. Doria, 6, 95125, Catania, Italy

    E. Rizzarelli & G. Vecchio

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  1. G. Maccarrone
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  2. E. Rizzarelli
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Editors and Affiliations

  1. Dipartimento di Chimica Generale, Università di Pavia, Pavia, Italy

    Luigi Fabbrizzi  & Antonio Poggi  & 

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Maccarrone, G., Rizzarelli, E., Vecchio, G. (1994). Chiral Recognition by Functionalized Cyclodextrin Metal Complexes. In: Fabbrizzi, L., Poggi, A. (eds) Transition Metals in Supramolecular Chemistry. NATO ASI Series, vol 448. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-8380-0_19

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  • DOI: https://doi.org/10.1007/978-94-015-8380-0_19

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