Cleavable surfactants

Patent metadata

Field	Value
Publication number	US-9816054-B2
Application number	US-24958408-A
Country	US
Kind code	B2
Filing date	Oct 10, 2008
Priority date	Oct 11, 2007
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

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.

First claim

What is claimed is:

1. A compound of formula I:

wherein:
Q is (C 1 -C 6 )alkyl, (C 6 -C 10 )aryl, (C 5 -C 10 )heteroaryl, or (C 6 -C 10 )aryl-NH(C 1 -C 6 )alkyl;
Y is —O—C(═Z)—X—;
Z is O or S;
A is aryl, aryl(C 1 -C 6 )alkyl, heteroaryl, or a direct bond;
X is O, NH, or S;
V is C;
M is H, an alkali metal, or tetra(C 1 -C 20 )alkylammonium;
L is —X—C(═Z)—X— or a direct bond;
R 1 is (C 6 -C 16 )aryl, or (C 5 -C 10 )heteroaryl;
R 2 and R 3 are each independently H or (C 10 -C 12 )alkyl;
wherein any alkyl, alkenyl, aryl, or heteroaryl, carbocyclic ring, or heterocyclic ring, is optionally substituted with one or more (e.g., 1, 2, 3, 4, or 5) (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, (C 2 -C 10 )alkynyl, (C 3 -C 10 )cycloalkyl, (C 1 -C 20 )alkoxy, (C 1 -C 20 )alkylcarbonyl, (C 1 -C 20 )alkylcarboxyl, halo, hydroxyl, —CO 2 R x , —SO 2 R x , —SO 3 R x , nitro, amino, N(R x ) 2 , mercapto, (C 1 -C 20 )alkylthio, (C 6 -C 16 )aryl, (C 6 -C 30 )arylthio, trifluoromethyl, ═O, heteroaryl, or heterocycle groups; provided that Q is not substituted with CO 2 H; and
each R x is independently H, (C 1 C 6 )alkyl, (C 6 -C 16 )aryl, or (C 1 C 6 )alkyl-(C 6 -C 16 )aryl; or a salt thereof; and
wherein R 2 and R 3 are not both H.

2. The compound of claim 1 wherein Q is (C 1 -C 6 )alkyl, phenyl, or phenyl-NH(C 1 -C 6 )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

a salt thereof.

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

7. The compound of claim 1 , wherein said (C 10 -C 12 )alkyl is a straight-chain C 10 -alkyl or a straight-chain C 12 -alkyl.

Assignees

• Saveliev Sergei
• Simpson Daniel
• Wood Keith V
• Uyeda Harry Tetsuo
• Hitko Carolyn Woodroofe
• Klaubert Dieter
• Promega Corp

Inventors

• Saveliev Sergei
• Simpson Daniel
• Wood Keith V
• Uyeda Harry Tetsuo
• Hitko Carolyn Woodroofe
• Klaubert Dieter

Classifications

• C11D1/20 Primary

  Fatty acid condensates · CPC title

• C07D307/40

  Radicals substituted by oxygen atoms · CPC title

• C07C329/06

  having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms · CPC title

• C07C309/16

  containing doubly-bound nitrogen atoms bound to the carbon skeleton · CPC title

• C07D317/22

  etherified · CPC title