Deoxycholate
 
Sodium deoxycholate, a bile acid salt, is a strongly denaturing, anionic detergent that is structurally close to sodium cholate. The 5-OH group of cholate is replaced with a hydrogen atom in deoxycholate (Fig. 1). This detergent has been used to solubilize many membrane-anchored proteins, such as those that are membrane-linked via a phosphatidylinositol-containing glycolipid (termed GPI-anchored proteins) (1, 2). Although it has rarely been shown that sodium deoxycholate solubilizes integral membrane proteins, certain insoluble, extracellular proteins, such as human lens membrane proteinase, have been efficiently solubilized by using sodium deoxycholate (3). Sodium deoxycholate has a relatively high critical micelle concentration (cmc) of ~10 mM, which makes it easy to be removed by dialysis from the solubilized proteins and lipids. Although this detergent is strongly denaturing toward integral membrane proteins, it solubilizes membrane lipids efficiently (4( and also stimultes G-protein-coupling to an effector, such as phospholipase C (5). 

Figure 1. The structure of sodium deoxycholate.
References
1. D. W. Loe, J. R. Glover, S. Head, and F. J. Sharom (1989) Biochem. Cell Biol. 67, 214–223. 
2. N. M. Hooper and A. J. Turner (1988) Biochem. J. 250, 865–869. 
3. O. P. Srivatsava and K. Srivatsava (1989) Exp. Eye Res. 48, 161–175. 
4. P. Banerjee J. B. Joo, J. T. Buse, and G. Dawson (1995) Chem. Phys. Lipids 77, 65–78. 
5. H. Nakanishi, Y. Takeyama, H. Ohyanagi, Y. Saitoh, and Y. Takai (1990) Biochem. Biophys. Res. Commun. 170, 111–118.