Co-operative intramolecular hydrogen bonding in glucose and maltose

Abstract

SIMPLE ¹H n.m.r. measurements of glucose, maltose, and some of their derivatives in dimethyl sulphoxide solution confirm the inter-residue 2′-OH ⋯ 3-OH hydrogen bond in maltose and reveal the presence of weaker intra-residue hydrogen bonds between vicinal hydroxy groups in both glucose and maltose. Co-operative stabilisation of intra-residue hydrogen bonding is provided by the participation of the anomeric hydroxy group in glucose and by the inter-residue 2′-OH-3 ⋯ OH hydrogen bond in maltose.