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US 8,263,754 B2Granted
Amphiphiles for protein solubilization and stabilization
AssigneesWisconsin Alumni Research Foundation, Uchicago Argonne, LLC
InventorsSamuel Helmer Gellman, Pil Seok Chae, Philip D. Laible, Marc J. Wander
Life of this patent
Estimating the term…
Abstract
The invention provides amphiphiles for manipulating membrane proteins. The amphiphiles can feature carbohydrate-derived hydrophilic groups and branchpoints in the hydrophilic moiety and/or in a lipophilic moiety. Such amphiphiles are useful as detergents for solubilization and stabilization of membrane proteins, including photosynthetic protein superassemblies obtained from bacterial membranes.
Claims22
An amphiphilic compound of Formula I:
- wherein
- each R is independently C1-C16 straight or branched alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, or C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- or
- the two R groups together with the carbon to which they are attached form a C3-C8 cycloalkyl, a C3-C8 cycloalkenyl, or an adamantyl ring;
- R1 is C1-C16 straight or branched alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, halophenyl, p-tolyl, adamantyl or C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, halophenyl, p-tolyl, adamantyl substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- or
- R, R, and R1 together with the carbon to which they are attached form an adamantyl ring, optionally substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- X is CH2 or a direct bond;
- R2 is H, an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two or more glycosyl residues;
- R3 is an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two or more glycosyl residues, or a C1-C4 alkyl-(N,N-dimethyl)N-oxide;
- and
- R4 is an O-linked C6 glycosyl residue, an O-linked oligosaccharide comprising two or more glycosyl residues, or a C1-C4 alkyl-(N,N-dimethyl)N-oxide.
9 more elements
An amphiphilic compound of Formula IV:
- wherein
- one R is H and the other R is C1-C16 straight or branched alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, or C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- or
- the two R groups together with the carbon to which they are attached form an adamantyl ring;
- R1 is C1-C16 straight or branched alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, halophenyl, p-tolyl, adamantyl or C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, halophenyl, p-tolyl, adamantyl substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- or
- R, R, and R1 together with the carbon to which they are attached form an adamantyl ring, optionally substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- each X is independently CH2 or a direct bond;
- R2 is H, an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two glycosyl residues;
- R3 is H, an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two glycosyl residues;
- and
- R4 is an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two glycosyl residues.
9 more elements
An amphiphilic compound wherein the compound is:
An amphiphilic compound of Formula VI:
- wherein R is H, C1-C16 straight or branched alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl, or C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, biphenyl substituted with one, two, or three C1-C6 straight or branched alkyl groups;
- each X is independently CH2 or a direct bond;
- R2 is H, an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two or more glycosyl residues;
- R3 is H, an O-linked C6 glycosyl residue, or an O-linked oligosaccharide comprising two or more glycosyl residues, or a C1-C4 alkyl-(N,N-dimethyl)N-oxide;
- and
- R4 is an O-linked C6 glycosyl residue, an O-linked oligosaccharide comprising two or more glycosyl residues, or a C1-C4 alkyl-(N,N-dimethyl)N-oxide.
3 more elements
Dependencies are inferred from the claim text.