Synthesis and properties of unsymmetrical aryl glucosyl disulfides: models for a new class of cleavable nonionic detergents

J Cuomo, JH Merrifield, JFW Keana

Index: Cuomo, John; Merrifield, James H.; Keana, John F.W. Journal of Organic Chemistry, 1980 , vol. 45, # 21 p. 4216 - 4219

Full Text: HTML

Citation Number: 40

Abstract

The purpose of this study was the synthesis and evaluation of the first members of a new series of unsymmetrical aryl glucosyl disulfides. Such cleavable molecules are potentially useful as solubilizing agents for membrane proteins. Unsymmetrical disulfides 6a-d were prepared as follows. The corresponding phenol was converted into the N, N- dimethylcarbamothioic acid ester (eg, 2a) which was rearranged thermally to the thioester ...