Amphiphiles for protein solubilization and stabilization

1. An amphiphilic compound of Formula VII:

wherein

Y is —CH 2 — or —NH(C 1 -C 4 alkyl)-;

Z is O or absent;

R 5 is H or a C 6 glycosyl residue; and

each R 6 is independently H or C 1 -C 6 alkyl.

2. The amphiphilic compound of claim 1 wherein Y is CH 2 or —NH(CH 2 —CH 2 )—.

3. The amphiphilic compound of claim 1 wherein Z is O.

4. The amphiphilic compound of claim 1 wherein R 5 is H.

5. The amphiphilic compound of claim 1 wherein R 5 is an O-linked glucose, mannose, galactose.

6. The amphiphilic compound of claim 1 wherein the compound is:

7. The amphiphilic compound of claim 1 wherein Z is absent.

8. The amphiphilic compound of claim 7 wherein Y is —CH 2 —.

9. The amphiphilic compound of claim 8 wherein R 5 is H.

10. The amphiphilic compound of claim 8 wherein R 5 is an O-linked glucose, mannose, galactose.

11. A method for solubilizing or stabilizing a membrane protein comprising contacting a protein in an aqueous environment with an effective amount of a compound of claim 1 , and optionally heating the protein and the compound, to provide the solubilized protein encapsulated in micelles of the compound.

12. An amphiphilic compound of Formula VIII:

wherein Y is —CH 2 —,

both R groups are C 1 -C 8 straight chain alkyl,

R 1 is phenyl,

—X—R 2 is direct bond-H, and

R 3 is H an O-linked C 6 glycosyl residue, an O-linked oligosaccharide comprising two or more glycosyl residues,or a C 1 -C 4 alkyl-(N,N-dimethyl)-oxide; and

R 4 is an O-linked C 6 glycosyl residue, an O-linked oligosaccharide comprising two or more glycosyl residues, or a C 1 -C 4 alkyl-(N,N-dimethyl)N-oxide provided that

one or both of R 3 and R 4 are O-linked glucose, mannose, galactose, maltose or sucrose residues or O-linked oligosaccharides comprising two or more glycosyl residues.

13. The amphiphilic compound of claim 12 wherein the compound is:

14. An amphiphilic compound of Formula VIII:

wherein

Y is C 1 -C 4 alkylene, —NH(C 1 -C 4 alkyl)-, or a direct bond;

Z is O or absent, provided that when Y is a direct bond, Z is O;

each R is independently C 1 -C 16 straight or branched alkyl C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, phenyl, biphenyl, or C 3 -C 8 cycloalkyl, C 3-C 8 cycloalkenyl, phenyl, or biphenyl substituted with one, two, or three C 1 -C 6 straight or branched alkyl groups; or

the two R groups together with the carbon to which they are attached form a C 3 -C 8 cycloalkyl, a C 3 -C 8 cycloalkenyl, or an adamanttyl ring;

R 1 is H, C 1 -C 16 straight or branched alkyl,C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, phenyl, biphenyl, halophenyol, p-tolyl, adamantyl or C 3 -C 8 cycloalkyl C 3 -C 8 cycloalkenyl, phenyl, biphenyl, halophenyl, p-tolyl, or adamantyl substituted with one two or three C 1 -C 6 straight or branched alkyl groups; or

R, R, and R 1 together with the carbon to which they are attached form an adamantyl ring, optionally substituted with one, two, or three C 1 -C 6 straight or branched alkyl groups;

each X is independently CH 2 or a direct bond;

R 2 is H, an O-linked C 6 glycosyl residue, an O-linked oligosaccharide comprising two or more glycosyl residues, or a C 1 - 4 alkyl-(N,N-dimethyl)N-oxide;

R 3 is H, an O-linked C 6 glycosyl residue, O-linked oligosaccharide comprising two or more glycosyl residue, or a C 1 -C 4 alkyl -(N,N-dimethyl)N-oxide; and

R 4 is an O-linked C 6 gylcosyl residue an O-linked oligosaccharide comprising two or more gylcosyl residues, or a C 1-C 4 alkyl-(N,N-dimethyl)N-oxide; provided that

one or both of R 3 and R 4 are C 1 -C 4 alkyl-(N,N-dimethyl)N-oxide.

15. The amphiphilic compound of claim 14 wherein the compound is:

16. A method for solubilizing or stabilizing a membrane protein comprising contacting a protein in an aqueous environment with an effective amount of a compound of claim 12 , and optionally heating the protein and the compound, to provide the solubilized protein encapsulated in micelles of the compound.