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Issue 9, 2009
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Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study

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Abstract

The stereoselectivity of the reaction between (R)-(−)-2-butylamine and the diastereomeric proton-bound complexes of (+)-catharanthine (C) or (−)-vindoline (V) with some chiral amido[4]resorcinarenes has been investigated in the gas phase by ESI-FT-ICR-MS. The reaction stereoselectivity (0.56 < khomo/khetero < 16.9) is found to depend critically on the functional groups present in the chiral pendants of the hosts. Rationalisation of the kinetic results is based on careful computational and spectroscopic studies of the most stable conformations of (+)-catharanthine and its protonated form in the isolated state and in water, as well as in a representative host structure. The emerging picture points to the relevant diastereomeric proton-bound complexes as quasi-degenerate, thus suggesting that their stereoselectivity in the guest exchange reaction is mostly due to kinetic factors. The results of this study may represent a starting point for a deeper comprehension of the intrinsic factors that endow these molecules, and their dimeric forms, with their biochemical properties.

Graphical abstract: Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study

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Publication details

The article was received on 15 Jan 2009, accepted on 29 Jan 2009 and first published on 04 Mar 2009


Article type: Paper
DOI: 10.1039/B900735K
Citation: Org. Biomol. Chem., 2009,7, 1798-1806
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    Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study

    B. Botta, C. Fraschetti, F. R. Novara, A. Tafi, F. Sacco, L. Mannina, A. P. Sobolev, J. Mattay, M. C. Letzel and M. Speranza, Org. Biomol. Chem., 2009, 7, 1798
    DOI: 10.1039/B900735K

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