Cleavable surfactants

• US 9,816,054 B2
• Filed: 10/10/2008
• Issued: 11/14/2017
• Est. Priority Date: 10/11/2007
• Status: Active Grant

• Current Assignee: Promega Corporation
• Original Assignee: Promega Corporation
• Inventors: Saveliev, Sergei, Simpson, Daniel, Wood, Keith V., Uyeda, Harry Tetsuo, Hitko, Carolyn Woodroofe, Klaubert, Dieter
• Primary Examiner(s): Haq, Shafiqul
• Application Number:
  US12/249,584
• Publication Number:
  US 20090095628A1
• Time in Patent Office: 3,322 Days
• CPC Class Codes: C07C 309/10 with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
• CPC Class Codes: C07C 309/14 containing amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 309/15 the nitrogen atom of at least one of the amino groups being part of any of the groups , X being a hetero atom, Y being any atom
• CPC Class Codes: C07C 309/16 containing doubly-bound nitrogen atoms bound to the carbon skeleton
• CPC Class Codes: C07C 323/12 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 329/06 having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
• CPC Class Codes: C07D 307/40 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 307/56 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 317/22 etherified
• CPC Class Codes: C07D 333/16 by oxygen atoms
• CPC Class Codes: C11D 1/143 Sulfonic acid esters
• CPC Class Codes: C11D 1/20 Fatty acid condensates

Abstract

The invention provides surfactant compounds of formulas I-IX, which can be used in methods for aiding the solubilization, digestion, preparation, analysis, and/or characterization of biological material, for example, proteins or cell membranes. The compounds can also aid in the recovery of peptides generated during protein digestion, particularly for in-gel digestion protocol. Additionally, the compounds can improve enzymatic protein deglycosylation without interfering with downstream sample preparation steps and mass spectrometric analysis. The compounds can be specifically useful as digestion aids that can be decomposed by an acid, by heat, or a combination thereof. Decomposition of the surfactants allows for facile separation from isolated samples, and/or allows for analysis of the sample without interfering with the sensitivity of various analytical techniques.

Claims

1. A compound of formula I:

2. The compound of claim 1 wherein Q is (C₁-C₆)alkyl, phenyl, or phenyl-NH(C₁-C₆)alkyl.

3. The compound of claim 1 wherein A is a direct bond.

4. The compound of claim 1 wherein V is C and L is a direct bond.

5. The compound of claim 1 wherein the compound is

6. A composition comprising a gel and a compound of claim 1.

7. The compound of claim 1, wherein said (C₁₀-C₁₂)alkyl is a straight-chain C₁₀-alkyl or a straight-chain C₁₂-alkyl.