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Intra‐ and Intermolecular H‐Bonds of Alcohols in DMSO, 1 H‐NMR Analysis of Inter‐Residue H‐Bonds in Selected Oligosaccharides: Cellobiose, Lactose, N , N ′‐Diacetylchitobiose, Maltose, Sucrose, Agarose, and Hyaluronates
Author(s) -
Bernet Bruno,
Vasella Andrea
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000906)83:9<2055::aid-hlca2055>3.0.co;2-c
Subject(s) - chemistry , cellobiose , maltose , residue (chemistry) , lactose , agarose , disaccharide , stereochemistry , sucrose , hydrogen bond , intermolecular force , organic chemistry , biochemistry , cellulase , enzyme , molecule
Inter‐residue H‐bonds of oligosaccharides in (D 6 )DMSO have been assigned on the basis of a combined interpretation of the chemical shift ( δ (OH)), coupling constant ( J (H,OH)), and temperature dependence ( Δ δ (OH)/ Δ T ) of OH signals. Cellobiose, lactose, and N , N ′‐diacetylchitobiose possess a completely persistent C(3)OH⋅⋅⋅OC(5′) H‐bond. Maltose is characterised 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 differently H‐bonded species, and hyaluronates possess four strong inter‐residue H‐bonds.