title: Solution structure of R(2)Sn(IV)-beta-N-acetyl-neuraminate (R = Me, Bu) complexes in D(2)O and DMSO-d(6): experimental NMR and DFT computational study.
abstract: 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.
authors: Dipartimento di Chimica Inorganica e Analitica Stanislao Cannizzaro, Università di Palermo, Viale delle Scienze Parco d'Orleans II, Ed.17, 90128, Palermo, Italy. bertazzi@unipa.it
authors: Nuccio
authors: N
authors: Bertazzi
authors: Girolamo
authors: G
authors: Casella
authors: Francesco
authors: F
authors: Ferrante
authors: Lorenzo
authors: L
authors: Pellerito
authors: Archimede
authors: A
authors: Rotondo
authors: Enrico
authors: E
authors: Rotondo
mesh_terms: D017666:Deuterium Oxide / Q000737:chemistry; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008432:Mathematical Computing; D015394:Molecular Structure; D009438:Neuraminic Acids / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D012794:Sialic Acids / Q000737:chemistry*; D012996:Solutions
chemical_list: D009438:Neuraminic Acids; D009947:Organotin Compounds; D012794:Sialic Acids; D012996:Solutions; C520976:dibutyl(N-acetylneuraminic acid)tin(IV); C520975:dimethyl(N-acetylneuraminic acid)tin(IV); D017666:Deuterium Oxide; D004121:Dimethyl Sulfoxide