Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5673
Title: Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic and spectroscopic study
Authors: Botta, Bruno
Fraschetti, Caterina
Novara, Francesca R.
Tafi, Andrea 
Sacco, Fabiola
Mannina, Luisa
Sobolev, Anatoli P.
Mattay, Jochen
Letzel, Matthias C.
Speranza, Maurizio
Issue Date: 2009
Project: None 
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
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 < k(homo)/k(hetero) < 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.
Description: 
19587
URI: http://hdl.handle.net/20.500.12779/5673
ISSN: 1477-0520
DOI: 10.1039/b900735k
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