Design and Synthesis of Bioactive Valienamine-type Chaperones

Valienamine (1) i s the unsaturated derivative of carbocyclic analogues of glycosylamines. I ts αand β-anomeric i somers ar e n ot i nterconvertible each o ther, existing as chemically stable forms (Fig. 1). Compound 1 was first isolated from antibiotic v alidamycins a nd f ound t o pos sess a s trong i nhibitory a ctivity a gainst α-glucosidase. It was also shown as one of the components of pseudo-tetrasaccharide, α-amylase inhibitor acarbose, which has been clinically important to control diabetes. Later, starting from valiolamine, the hydrated form of 1, potent α-glucosidase inhibitor voglibose has been developed and widely used equally as acarbose.