The Conformational Behaviour of Non-Hydrolizable Lactose Analogues: The Thioglycoside, Carbaglycoside, and Carba-Iminoglycoside Cases

Abstract

The conformational behaviours of several nonhydrolizable lactose analogues, namely methyl α-thiolactoside (1), methyl β-carbalactoside (2) and methyl β-carbaiminolactoside (3) have been studied using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations. Analogies and differences with the natural compounds have been found.