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Issue 16, 2011
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Transformations of the natural cytokinin N6-isopentenyladenine in aqueous acidic media: structural aspects

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Abstract

N6-Isopentenyladenine (L1) was subjected to variously acidic media in 0.1 M, 1 M and 2 M HCl. In dependence on the acidity of the medium, the formation of three main acid hydrolysis products, involving the N6-isopentenyladeninium (HL1) (1), 7,8,9,10-tetrahydro-7,7-dimethyl-3H-pyrimido[2,1-i]purin-6-ium (HL2) (2) or 5-amino-4-(4,4-dimethyl-3,4,5,6-tetrahydropyrimidin-2-yl)-imidazolium (H2L3) (3–5) cations, were determined and characterized by multinuclear solution-state NMR spectroscopy and in the solid state by single crystal X-ray analysis. The coordination abilities of these transformation products have been also investigated. The compounds of the compositions [Zn(HL1)Cl3]·H2O (1), [Zn3(HL2)2Cl8] (2), (H2L3)[CuCl4] (4) and (H2L3)[ZnCl4] (5) have been prepared in dependence on the acidity of the medium used by the reactions of L1 with ZnCl2·1.5H2O or CuCl2·2H2O. Based on the NMR spectroscopic and X-ray crystallographic results, the mechanism of transformation of L1 in the acidic medium, involving the protonation, cyclization and ring fission, has been suggested.

Graphical abstract: Transformations of the natural cytokinin N6-isopentenyladenine in aqueous acidic media: structural aspects

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Supplementary files

Article information


Submitted
26 Apr 2011
Accepted
16 May 2011
First published
16 May 2011

Org. Biomol. Chem., 2011,9, 5703-5713
Article type
Paper

Transformations of the natural cytokinin N6-isopentenyladenine in aqueous acidic media: structural aspects

Z. Trávníček, R. Novotná, J. Marek, I. Popa and M. Šipl, Org. Biomol. Chem., 2011, 9, 5703 DOI: 10.1039/C1OB05649B

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