Improved Synthesis ofn-octyl-β-D-Glucoside: A Nonionic Detergent of Considerable Potential in Membrane Biochemistry
- 1 January 1978
- journal article
- research article
- Published by Taylor & Francis in Membrane Biochemistry
- Vol. 1 (3-4) , 323-327
- https://doi.org/10.3109/09687687809063854
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.Keywords
This publication has 10 references indexed in Scilit:
- Newer observations on the synthesis of O-glycosidesPublished by Springer Nature ,2006
- Solubilization of membranes by detergentsPublished by Elsevier ,2003
- Characterization of membrane proteins in detergent solutionsBiochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 1976
- Alkyl glucosides as effective solubilizing agents for bovine rhodopsin. A comparison with several commonly used detergentsBiochimica et Biophysica Acta (BBA) - Biomembranes, 1976
- Reconstitution of D-glucose transport catalyzed by a protein fraction from human erythrocytes in sonicated liposomes.Proceedings of the National Academy of Sciences, 1976
- Solubilization of bacterial membrane proteins using alkyl glucosides and dioctanoyl phosphatidylcholineBiochimica et Biophysica Acta (BBA) - Biomembranes, 1975
- Nuclear magnetic resonance in carbohydrate chemistryChemical Reviews, 1973
- SUBSTITUTIONAL AND CONFIGURATIONAL EFFECTS ON CHEMICAL SHIFT IN PYRANOID CARBOHYDRATE DERIVATIVESCanadian Journal of Chemistry, 1965
- The Surface Tension and the Critical Micelle Concentration in Aqueous Solution of β-d-Alkyl Glucosides and their MixturesBulletin of the Chemical Society of Japan, 1961
- The Preparation of Some Higher AlkylglucosidesJournal of the American Chemical Society, 1938