Destructible surfactants and uses thereof
View Patent ↗Destructible surfactants and methods of using same are provided. The invention includes anionic surfactants having a dioxolane or dioxane functional group which enables the surfactant to be broken down under acidic conditions. The invention also includes methods of making anionic surfactants and methods of using anionic surfactants in a variety of applications.
1. A method for performing electrophoresis comprising contacting a sample with a surfactant represented by the formula (Formula I):
in which
p is 0, 1 or 2;
R is alkyl;
R 1 and R 2 are each, independently, hydrogen or methyl; and
R 3 is selected from —OSO 3 − , —R 4 OSO 3 − , —R 4 OR 5 SO 3 − , and —OR 5 SO 3 − ,
wherein R 4 and R 5 are each, independently, lower alkyl; to form a sample/surfactant complex,
performing electrophoresis on the sample/surfactant complex.
2. The method of claim 1 comprising the further step of degrading the surfactant after electrophoresis.
3. The method of claim 2 wherein the step of degrading the surfactant after electrophoresis comprises contacting the surfactant with an acidic solution.
4. The method of claim 2 comprising the further step of purifying the sample.
5. The method of claim 1 wherein the surfactant is represented by the following formula:
in which
R 6 is alkyl;
R 7 is selected from —OSO 3 − , —R 4 OSO 3 − , —R 4 OR 5 SO 3 − , and —OR 5 SO 3 − ,
wherein R 4 and R 5 are each, independently, lower alkyl.
6. The method of claim 1 wherein the surfactant has the following chemical structure:
7. The method of claim 1 wherein the surfactant has the following chemical structure:
8. A kit for performing electrophoresis comprising:
a surfactant represented by the formula:
in which
p is 0, 1 or 2;
R is alkyl;
R 1 and R 2 are each, independently, hydrogen or methyl; and
R 3 is selected from OSO 3 − , R 4 OSO 3 − , and OR 5 OSO 3 − , wherein R 4 and R 5 are each, independently, lower alkyl, and
at least one further component selected from the group consisting of a molecular weight standard, a staining reagent and a solution for degrading the surfactant.
9. The kit of claim 8 comprising a solution for degrading the surfactant.
10. The kit of claim 8 wherein the surfactant is represented by the following formula:
in which
R 6 is alkyl;
R 7 is selected from —OSO 3 − , —R 4 OSO 3 − , —R 4 OR 5 SO 3 − , and —OR 5 SO 3 − ,
wherein R 4 and R 5 are each, independently, lower alkyl.
11. The kit of claim 8 wherein the surfactant has the following chemical structure:
12. The kit of claim 8 wherein the surfactant has the following chemical structure:
13. A method for analyzing a sample comprising first contacting a sample with a surfactant represented by the formula:
in which
p is 0, 1 or 2;
R is alkyl;
R 1 and R 2 are each, independently, hydrogen or methyl; and
R 3 is selected from —OSO 3 − , —R 4 OSO 3 − , —R 4 OR 5 SO 3 − , and —OR 5 SO 3 − ,
wherein R 4 and R 5 are each, independently, lower alkyl; and analyzing the sample.
14. The method of claim 13 wherein the step of analyzing the sample comprises high performance liquid chromatography.
15. The method of claim 13 wherein the step of analyzing the sample comprises mass spectrometric detection.
16. The method of claim 13 wherein the step of analyzing the sample comprises ion-pair liquid chromatography.
17. A surfactant having the following chemical structure:
18. A method of synthesizing a surfactant represented by the formula:
in which
p is 0, 1 or 2;
R is alkyl;
R 1 and R 2 are each, independently, hydrogen or methyl;
R 3 is selected from —OSO 3 − , —R 4 OSO 3 − , —R 4 OR 5 SO 3 − , and —OR 5 SO 3 − ,
wherein R 4 and R 5 are each, independently, lower alkyl;
with the provisos that when p is 0 and R 1 is methyl, R 3 is not —CH 2 O(CH 2 ) 4 SO 3 or when p is 1 and R 1 is hydrogen and R 2 is methyl, R 3 is not —CH 2 OSO 3 ;
the method comprising the step of reacting a compound represented by the formula:
wherein R, R 1 and R 2 are defined as above and R 8 is hydroxyl or —CH 2 OH, with a compound represented selected from sulfites,
and
19. A method of solubilizing a substance comprising contacting a substance with a surfactant represented by the formula (Formula I):
in which
p is 0, 1 or 2;
R is alkyl;
R 1 and R 2 are each, independently, hydrogen or methyl; and
R 3 is selected from OSO 3 − , R 4 OSO 3 − , and OR 5 OSO 3 − , wherein R 4 and R 5 are each, independently, lower alkyl and
said substance selected from the group consisting of inclusion bodies, lipophilic proteins, receptors, membrane bound proteins, and biological tissues.
20. A method of regenerating a liquid chromatography column having a sorbent comprising contacting the sorbent with a surfactant represented by the formula (Formula I):
in which
p is 0, 1 or 2;
R is alkyl;
R 1 and R 2 are each, independently, hydrogen or methyl; and
R 3 is selected from —OSO 3 − , —R 4 OSO 3 − , —R 4 OR 5 SO 3 − , and —OR 5 SO 3 − ,
wherein R 4 and R 5 are each, independently, lower alkyl.