Sulfobetaine derivatives of bile acids: nondenaturing surfactants for membrane biochemistry.
The syntheses of four new sulfobetaine derivatives of bile salts are presented, along with a general set of criteria for useful detergents in membrane biochemistry. Physical properties including the critical micelle concentration, aggregation number, partial specific volume, critical micellar temperature, uv-vis spectrum, and circular dichroism spectrum are examined for the new compounds. To examine the interaction of this class of compounds with macromolecules, one of these (CHAPS) was further studied. Circular dichroism spectra of apolipoprotein C-III2 were measured in the presence of varying concentrations of CHAPS to determine the effect of this compound on secondary structure. Gel-exclusion chromatography and sedimentation equilibrium studies of cytochrome P-450 in the presence of CHAPS were also performed to establish the ability of this detergent to disaggregate cytochrome P-450 to a monomeric/dimeric state.
D053305:Apolipoprotein C-III; D001053:Apolipoproteins / Q000032:analysis; D001056:Apolipoproteins C; D001622:Betaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D001647:Bile Acids and Salts; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002793:Cholic Acids; D003577:Cytochrome P-450 Enzyme System / Q000032:analysis; D003902:Detergents / Q000138:chemical synthesis*; D008566:Membranes / Q000737:chemistry*; D008823:Micelles; D013500:Surface Tension; D013501:Surface-Active Agents / Q000138:chemical synthesis*
D053305:Apolipoprotein C-III; D001053:Apolipoproteins; D001056:Apolipoproteins C; D001647:Bile Acids and Salts; D002793:Cholic Acids; D003902:Detergents; D008823:Micelles; D013501:Surface-Active Agents; D001622:Betaine; D003577:Cytochrome P-450 Enzyme System; C028213:3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate