6533b7d8fe1ef96bd126996d

RESEARCH PRODUCT

Solution structure of R2Sn(IV)-β-N-Acetyl-Neuraminate (R=Me, Bu) complexes in D2O and DMSO-d6: experimental NMR and DFT computational study.

Archimede RotondoEnrico RotondoFrancesco FerranteNuccio BertazziGirolamo CasellaLorenzo Pellerito

subject

Magnetic Resonance SpectroscopyDenticityMolecular StructureStereochemistrychemistry.chemical_elementNuclear magnetic resonance spectroscopyMedicinal chemistrySolutionsInorganic Chemistrychemistry.chemical_compoundchemistryAlkoxideOrganotin CompoundsSialic AcidsSide chainDimethyl SulfoxideNeuraminic AcidsChelationCarboxylateNMR structural characterization; Alkyltin(IV); N-acetilneuraminic acid; DFT theroretical calculationsDeuterium OxideTinMathematical ComputingVicinalNMR DFT sialic acid

description

Two diorganotin(IV)-NANA complexes (NANA (1) = beta-N-acetyl-Neuraminic Acid = 5-amino-3,5-dideoxy-D-glycero-beta-D-galactononulosic acid) with formula Me(2)Sn(iv)NANA (2) and Bu(2)Sn(IV)NANA (3) were synthesized and characterized by (1)H, (13)C and (119)Sn NMR spectroscopy, both in D(2)O and DMSO-d(6) solutions. The experimental data in DMSO suggested the monosaccharide bidentate chelation via O1 carboxylate and vicinal O2 alkoxide atoms, which, in D(2)O, 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.

yearjournalcountryeditionlanguage
2007-03-28
10.1039/b616330khttp://hdl.handle.net/10447/32542