Synthetic amphiphiles for membrane protein manipulation
AssigneeWisconsin Alumni Research Foundation
InventorsSamuel Helmer Gellman, Pil Seok Chae, Brian Kobilka, Soren Rasumssen
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Abstract
The invention provides amphiphilic compounds and methods for manipulating membrane proteins. Compounds of the invention, for example, the compounds of Formulas I-XIX, can be prepared from readily available starting materials. The amphiphilic compounds can manipulate membrane protein at relatively low concentrations compared to many known detergents. The compounds can be used to aid the isolation of membrane proteins, for example, to aid their solubilization and/or purification. The compounds can also be used to aid the functional and structural determination of membrane proteins, including their stabilization and crystallization.
Claims12
A compound of Formula I:
- wherein
- R1=R2=(C3-C20)cycloalkyl(C1-C20)alkyl;
- each X is independently —O—, —S—, —CH2—, —C(═O)NH—, or a direct bond;
- P1 is a disaccharide, —N(R3)-monosaccharide, —N(R3)-disaccharide, or —Y—(C1-C6)alkyl-Z;
- P2 is a disaccharide, —N(R3)-monosaccharide, —N(R3)-disaccharide, or —Y—(C1-C6)alkyl-Z;
- each Y is independently —C(═O)NH—, —CH2—, or a direct bond;
- each Z is independently —N+(O−)(Me)2, —OP(═O)(O−)—(C1-C6)alkyl-N((C1-C3)alkyl)3, —N+(Me)2-(C1-C6)alkyl-SO3−, or —N+(Me)2-(C1-C6)alkyl-CO2−;
- and
- each R3 is independently hydrogen or (C1-C6)alkyl optionally substituted with a hydroxy group.
A compound of Formula I:
- wherein
- R1=R2=cyclohexyl(C1-C20)alkyl;
- each X is independently —O—, —S—, —CH2—, —C(═O)NH—, or a direct bond;
- P1 is a monosaccharide, a disaccharide, —N(R3)-monosaccharide, —N(R3)-disaccharide, or —Y—(C1-C6)alkyl-Z;
- P2 is a monosaccharide, a disaccharide, —N(R3)-monosaccharide, —N(R3)-disaccharide, or —Y—(C1-C6)alkyl-Z;
- each Y is independently —C(═O)NH—, —CH2—, or a direct bond;
- each Z is independently —N+(O−)(Me)2, —OP(═O)(O−)—(C1-C6)alkyl-N((C1-C3)alkyl)3, —N+(Me)2-(C1-C6)alkyl-SO3−, or —N+(Me)2-(C1-C6)alkyl-CO2−;
- and
- each R3 is independently hydrogen or (C1-C6)alkyl optionally substituted with a hydroxy group.
The compound:
The compound:
The compound:
Dependencies are inferred from the claim text.