Improved Synthesis of n-octyl-β-D-Glucoside: A Nonionic Detergent of Considerable Potential in Membrane Biochemistry

Abstract

An improved synthesis for the nonionic detergent n-octyl-β-D-glucoside (detergent 2) is described. The key modification over earlier methods is the utilization of n-octyl alcohol as the limiting reagent in the condensation between bromide 1 and n-octyl alcohol. A 60-70% overall yield of 2 is obtained without isolation of the intermediate. The β-configuration at the anomeric carbon atom of 2 was confirmed by 100 mHz NMR spectroscopy.

Key Words:

• Nonionic detergent
• membrane protein
• synthesis
• n-octyl-β-D-glucoside