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Issue 14, 2007
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Solution structure of R2Sn(iv)-β-N-acetyl-neuraminate (R = Me, Bu) complexes in D2O and DMSO-d6: Experimental NMR and DFT computational study

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Abstract

Two diorganotin(IV)–NANA complexes (NANA (1) = β-N-acetyl-Neuraminic Acid = 5-amino-3,5-dideoxy-D-glycero-β-D-galactononulosic acid) with formula Me2Sn(IV)NANA (2) and Bu2Sn(IV)NANA (3) were synthesized and characterized by 1H, 13C and 119Sn NMR spectroscopy, both in D2O and DMSO-d6 solutions. The experimental data in DMSO suggested the monosaccharide bidentate chelation via O1 carboxylate and vicinal O2 alkoxide atoms, which, in D2O, can be dynamically extended to a third binding site (O8 atom) of the pendant chain. Coordination at the tin atom is discussed on the basis of experimental NMR data and DFT calculation.

Graphical abstract: Solution structure of R2Sn(iv)-β-N-acetyl-neuraminate (R = Me, Bu) complexes in D2O and DMSO-d6: Experimental NMR and DFT computational study

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Publication details

The article was received on 08 Nov 2006, accepted on 14 Feb 2007 and first published on 08 Mar 2007


Article type: Paper
DOI: 10.1039/B616330K
Dalton Trans., 2007, 1440-1446

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    Solution structure of R2Sn(IV)-β-N-acetyl-neuraminate (R = Me, Bu) complexes in D2O and DMSO-d6: Experimental NMR and DFT computational study

    N. Bertazzi, G. Casella, F. Ferrante, L. Pellerito, A. Rotondo and E. Rotondo, Dalton Trans., 2007, 1440
    DOI: 10.1039/B616330K

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