Non-ionic acid-labile surfactants and methods of use
A compound may generally comprise the formula: wherein R 1 is independently selected from C 2 -C 10 alkyl or substituted alkyl, R 2 is independently selected from the group consisting of —H and C 1 -C 6 alkyl or substituted alkyl, X is selected from the group consisting of —NH— and —O—, Y is a carbohydrate, and m is an integer from 1 to 8. The compound may comprise a non-ionic acid labile surfactant. The compound may be used to facilitate solubilization of proteins and other molecules in an aqueous environment.
1. A method comprising:
mixing a solvent and a non-ionic acid-labile surfactant of the formula:
wherein R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is selected from —(CH 2 ) 0-2 CH 3 alkyl, X is selected from the group consisting of —NH— and —O—, Y is a sugar, and m is an integer from 1 to 4;
contacting a sample and the mixture to generate a sample-surfactant complex; and
cleaving the non-ionic acid-labile surfactant to generate cleavage by-products.
2. The method of claim 1 comprising adjusting the sample to pH 6-12.
3. The method of claim 1 comprising isolating the sample from the cleavage by-products.
4. The method of claim 1 , comprising performing mass spectrometry on the isolated sample.
5. The method of claim 1 , wherein the cleaving comprises adjusting the sample-surfactant complex to pH 2-3 and incubating the sample-surfactant complex for 10-30 minutes at 4-50° C.
6. The method of claim 1 , wherein the solvent has a pH in the range of 7 to 10.
7. The method of claim 1 , comprising performing electrokinetic transport of the sample-surfactant complex.
8. The method of claim 1 , comprising performing enzymatic digestion of the sample-surfactant complex.
9. The method of claim 1 , wherein the non-ionic acid labile surfactant has the formula:
wherein R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is selected from —(CH 2 ) 0-2 CH 3 alkyl, X is selected from the group consisting of —NH— and —O—, Y is selected from the group consisting of a monosaccharide, a disaccharide, an oligosaccharide, and a polysaccharide, and m is an integer from 1 to 4.
10. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a monosaccharide, and m is 1.
11. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a disaccharide, and m is 1.
12. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a trisaccharide, and m is 1.
13. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a tetrasaccharide, and m is 1.
14. The method of claim 1 , wherein in the non-ionic acid labile surfactant Y is one of a disaccharide, an oligosaccharide, and a polysaccharide comprising a cellobiose unit, a galactose unit, a glucose unit, a glucosamine unit, a fructose unit, a lactose unit, a maltose unit, a mannose unit, a sucrose unit, and combinations thereof.
15. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a disaccharide comprising a maltose unit, and m is 1.
16. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a disaccharide comprising a glucose unit, and m is 1.
17. The method of claim 1 , wherein in the non-ionic acid labile surfactant R 1 is selected from —(CH 2 ) 2-7 CH 3 alkyl, R 2 is —CH 3 , Y is a disaccharide comprising glucose units, and m is 1.
18. The method of claim 1 , wherein in the non-ionic acid labile surfactant X is —NH—.
19. The method of claim 1 , wherein in the non-ionic acid labile surfactant X is —O—.
20. The method of claim 1 , wherein the non-ionic acid labile surfactant comprises N-[2,2-Bis(pentyloxy)propan-1-aminocarbonyl]-β-maltosylamine having the formula:
21. The method of claim 1 , wherein the non-ionic acid labile surfactant comprises N-[2,2-Bis(hexyloxy)propan-1-aminocarbonyl]-β-maltosylamine having the formula:
22. The method of claim 1 , wherein the non-ionic acid labile surfactant comprises N-[2,2-Bis(pentloxy)propan-1-oxycarbonyl]-β-maltosylamine having the formula:
23. The method of claim 1 , wherein the non-ionic acid labile surfactant comprises N-[2,2-Bis(hexyloxy)propan-1-oxycarbonyl]-β-maltosylamine having the formula:
24. The method of claim 1 , wherein the non-ionic acid labile surfactant has the formula:
wherein R 1 may be independently selected from C 2 -C 10 alkyl or substituted alkyl.
25. The method of claim 1 , wherein the non-ionic acid labile surfactant has the formula:
wherein R 1 may be independently selected from C 2 -C 10 alkyl or substituted alkyl.