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

Content Provider	Royal Society of Chemistry (RSC)
Author	Mattay, Jochen Tafi, Andrea Sobolev, Anatoli P. Mannina, Luisa Speranza, Maurizio Botta, Bruno Fraschetti, Caterina Novara, Francesca R. Sacco, Fabiola Letzel, Matthias C.
Copyright Year	2009
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.
Starting Page	1798
Ending Page	1806
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	9
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b900735k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Stereoselectivity Vindoline Catharanthine Chirality
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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