Acid labile surfactants
AssigneeWaters Technologies Corporation
InventorDarryl W. Brousmiche
Life of this patent
Estimating the term…
Abstract
This invention relates to an acid labile surfactant. In particular, the surfactants of the present invention include a dioxolane or dioxane functional group which enables the surfactant to hydrolyze in an acidic environment. Surfactants of this type can be utilized to enhance protein solubilization/enzyme digestion. Following hydrolysis to destroy the surfactant (which may chromatographic issues), there are generally two components formed—a hydrophilic one, and a hydrophobic one. By altering the chemistry of the hydrolysable linker, the polarity of the hydrophobic residue can be altered, allowing it to be solubilized by significantly less organic solvent, and to minimize the potential loss of peptide material and to expand the chromatographic conditions that can be utilized.
Claims29
A method for performing protein solubilization or enzyme digestion comprising contacting a sample with a surfactant represented by the Formula I:
- in which
- p and q are each, independently, 0, 1, or 2, and p+q is 1, 2, or 3;
- Ra and Rb are each, independently, alkyl, alkenyl, or alkynyl, and Ra is linear or branched C5-C30, and Rb is linear or branched C1-C5;
- X is CR′2, O, NR′, or S;
- wherein each R′ is independently H, lower alkyl, lower alkenyl, or lower alkynyl;
- R1 and R2 are each, independently, hydrogen or linear or branched C1-C5;
- and
- R3 is a group selected from —R4SO3−, —R4OR5SO3−, —R4(OCH2CH2)nSO3−, —R4OR5COO−, —R4CONCH3CH2COO−, —R4(OCH2CH2)nOP(OH)O2−, —R4OP(OH)O2−, —R4OP(OH)2O−, —R4OR5P(OH)2O−, —R4OR5OP(OH)2O−, —R4OR5N(R6)3+, —R4N+(CH3)2CH2COO−, or —R4N(CH3)3+R5SO3−;
- wherein R4, R5, and R6 are each, independently, lower alkyl, lower alkenyl, lower alkynyl, substituted lower alkyl, substituted lower alkenyl, or substituted lower alkynyl;
- n is 1 to 6.
A method for performing protein solubilization or enzyme digestion comprising contacting a sample with a surfactant that is represented by the following formula:
- in which
- Ra and Rb are each, independently, alkyl, alkenyl, or alkynyl, and Ra is linear or branched C5-C30, and Rb is linear or branched C1-C5;
- X is CR′2, O, NR′, or S;
- wherein each R′ is independently H, lower alkyl, lower alkenyl, or lower alkynyl;
- R1 and R2 are each, independently, hydrogen or linear or branched C1-C5;
- and
- R3 contains an anionic, a cationic, a zwitterionic, or a non-ionic hydrophilic group;
- to form a sample/surfactant complex.
A surfactant having the following chemical structure:
- in which
- p and q are each, independently, 0, 1, or 2, and p+q is 1, 2, or 3;
- Ra and Rb are each, independently, alkyl, alkenyl, or alkynyl, and Ra is linear or branched C5-C30, and Rb is linear or branched C1-C5;
- X is CR′2, O, NR′, or S;
- wherein each R′ is independently H, lower alkyl, lower alkenyl, or lower alkynyl;
- R1 and R2 are each, independently, hydrogen or linear or branched C1-C5;
- and
- R3 is a group selected from —R4SO3−, —R4OR5SO3−, —R4(OCH2CH2)nSO3−, —R4OR5COO−, —R4CONCH3CH2COO−, —R4(OCH2CH2)nOP(OH)O2−, —R4OP(OH)O2−, —R4OP(OH)2O−, —R4OR5P(OH)2O−, —R4OR5OP(OH)2O−, —R4OR5N(R6)3+, —R4N+(CH3)2CH2COO−, or —R4N(CH3)3+R5SO3−;
- wherein R4, R5, and R6 are each, independently, lower alkyl, lower alkenyl, lower alkynyl, substituted lower alkyl, substituted lower alkenyl, or substituted lower alkynyl;
- n is 1 to 6.
A surfactant represented by the following formula:
- in which
- Ra and Rb are each, independently, alkyl, alkenyl, or alkynyl, and Ra is linear or branched C5-C30, and Rb is linear or branched C1-C5;
- X is CR′2, O, NR′, or S;
- wherein each R′ is independently H, lower alkyl, lower alkenyl, or lower alkynyl;
- R1 and R2 are each, independently, hydrogen or linear or branched C1-C5;
- and
- R3 contains an anionic, a cationic, a zwitterionic, or a non-ionic hydrophilic group.
Dependencies are inferred from the claim text.