Intra- and intermolecular H-bonds of alcohols in DMSO - H-1-NMR analysis of inter-residue H-bonds in selected oligosaccharides: Cellobiose, lactose, N,N '-diacetylchitobiose, maltose, sucrose, agarose, and hyaluronates

Inter-residue H-bonds of oligosaccharides in (D-6)DMSO have been assigned o n the basis of a combined interpretation of the chemical shift (delta(OH)), coupling constant (J(H,OH)), and temperature dependence (Delta delta(OH)/D elta T) of OH signals. Cellobiose, lactose, and N,N'-diacetylchitobiose pos sess a completely persistent C(3)OH ... OC(.5') H-bond. Maltose is characte rised by flip-flop H-bonds between HO-C(3) and HO-C(2'), and agarose by two weakly persistent inter-residue H-bonds. Sucrose forms an equilibrium of d ifferently H-bonded species, and hyaluronates possess four strong inter-res idue H-bonds.