Cleavable detergents, also known as cleavable surfactants, are special surfactant

Surfactant

Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...

s (detergents) that are used in biochemistry

Biochemistry

Biochemistry, sometimes called biological chemistry, is the study of chemical processes in living organisms, including, but not limited to, living matter. Biochemistry governs all living organisms and living processes...

 and especially in proteomics

Proteomics

Proteomics is the large-scale study of proteins, particularly their structures and functions. Proteins are vital parts of living organisms, as they are the main components of the physiological metabolic pathways of cells. The term "proteomics" was first coined in 1997 to make an analogy with...

 to enhance protein

Protein

Proteins are biochemical compounds consisting of one or more polypeptides typically folded into a globular or fibrous form, facilitating a biological function. A polypeptide is a single linear polymer chain of amino acids bonded together by peptide bonds between the carboxyl and amino groups of...

 denaturation

Denaturation (biochemistry)

Denaturation is a process in which proteins or nucleic acids lose their tertiary structure and secondary structure by application of some external stress or compound, such as a strong acid or base, a concentrated inorganic salt, an organic solvent , or heat...

 and solubility. The detergent is rendered inactive by cleavage, usually under acid

Acid

An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...

ic conditions, in order to make the sample compatible with a following procedure or in order to selectively remove the cleavage products.

Applications for cleavable detergents include protease

Protease

A protease is any enzyme that conducts proteolysis, that is, begins protein catabolism by hydrolysis of the peptide bonds that link amino acids together in the polypeptide chain forming the protein....

 digestion

Digestion

Digestion is the mechanical and chemical breakdown of food into smaller components that are more easily absorbed into a blood stream, for instance. Digestion is a form of catabolism: a breakdown of large food molecules to smaller ones....

 of protein

Protein

Proteins are biochemical compounds consisting of one or more polypeptides typically folded into a globular or fibrous form, facilitating a biological function. A polypeptide is a single linear polymer chain of amino acids bonded together by peptide bonds between the carboxyl and amino groups of...

s such as in-gel digestion

In-gel digestion

The in-gel digestion is part of the sample preparation for the mass spectrometric identification of proteins in course of proteomic analysis. The method was introduced 1992 by Rosenfeld...

 with trypsin

Trypsin

Trypsin is a serine protease found in the digestive system of many vertebrates, where it hydrolyses proteins. Trypsin is produced in the pancreas as the inactive proenzyme trypsinogen. Trypsin cleaves peptide chains mainly at the carboxyl side of the amino acids lysine or arginine, except when...

 after SDS PAGE and peptide

Peptide

Peptides are short polymers of amino acid monomers linked by peptide bonds. They are distinguished from proteins on the basis of size, typically containing less than 50 monomer units. The shortest peptides are dipeptides, consisting of two amino acids joined by a single peptide bond...

 extractions from electrophoresis

Electrophoresis

Electrophoresis, also called cataphoresis, is the motion of dispersed particles relative to a fluid under the influence of a spatially uniform electric field. This electrokinetic phenomenon was observed for the first time in 1807 by Reuss , who noticed that the application of a constant electric...

 gels. Cleavable detergents are mainly used in sample preparations for mass spectrometry

Mass spectrometry

Mass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...

.

PPS

PPS, available as PPS Silent Surfactant from Protein Discovery, is the abbreviation for sodium 3-(4-(1,1-bis(hexyloxy)ethyl)pyridinium-1-yl)propane-1-sulfonate. This acetal

Acetal

An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...

ic detergent is split under acidic conditions into hexanol

Hexanol

Hexanol may refer to any of the following 17 isomeric organic compounds with the formula C6H13OH:...

 and the zwitterion

Zwitterion

In chemistry, a zwitterion is a neutral molecule with a positive and a negative electrical charge at different locations within that molecule. Zwitterions are sometimes also called inner salts.-Examples:...

ic 3-acetyl-1-(3-sulfopropyl)pyridinium.

2

ProteaseMAX

ProteaseMAX is the brandname of Promega

Promega

Promega Corporation is a manufacturer of enzymes and other products for biotechnology and molecular biology.-History :Promega Corporation was founded by Bill Linton in 1978 to provide restriction enzymes for biotechnology...

 for sodium 3-((1-(furan-2-yl)undecyloxy)carbonylamino)propane-1-sulfonate. This cleavable detergent is sensitive to heat and acid

Acid

An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...

 and is degraded during a typical trypsin digestion into the uncharged lipophilic

Lipophilic

Lipophilicity, , refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. These non-polar solvents are themselves lipophilic — the axiom that like dissolves like generally holds true...

 compound 1-(furan-2-yl)undecan-1-ol

1-(Furan-2-yl)undecan-1-ol

1-undecan-1-ol is an uncharged lipophilic degradation product of the surfactant ProteasMAX.- External links :*...

 and the zwitterion

Zwitterion

In chemistry, a zwitterion is a neutral molecule with a positive and a negative electrical charge at different locations within that molecule. Zwitterions are sometimes also called inner salts.-Examples:...

ic 3-aminopropane-1-sulfonic acid (homotaurine), which can be removed by C18 solid phase extraction

Solid phase extraction

Solid-phase extraction is a separation process by which compounds that are dissolved or suspended in a liquid mixture are separated from other compounds in the mixture according to their physical and chemical properties. Analytical laboratories use solid phase extraction to concentrate and purify...

 during sample work-up.

RapiGest SF

RapiGest SF is an acid-cleavable anionic detergent marketed by Waters Corporation

Waters Corporation

Waters Corporation is a publicly traded laboratory analytical instrument and software company headquartered in Milford, Massachusetts. The company employs more than 5,000 people, with manufacturing facilities located in Milford, Taunton, Massachusetts; Wexford, Ireland; Manchester, England; and...

. No information about its chemical structure has been published.

Others

MALDI matrix compounds such as α-cyano-4-hydroxycinnamic acid

Alpha-Cyano-4-hydroxycinnamic acid

α-Cyano-4-hydroxycinnamic acid, also written as alpha-cyano-4-hydroxycinnamic acid and abbreviated CHCA, is a cinnamic acid derivative and is a member of the phenylpropanoid family. It is used as a matrix for peptides and nucleotides in MALDI mass spectrometry analyses....

 have been linked through a linker consisting of an unsymmetric formaldehyde

Formaldehyde

Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...

 acetal

Acetal

An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...

s to dodecanol

Dodecanol

Dodecanol, also known by its IUPAC name 1-dodecanol or dodecan-1-ol, and by its trivial name dodecyl alcohol and lauryl alcohol, is a fatty alcohol. Dodecanol is a colourless, water insoluble solid of melting point 24 °C and boiling point 259 °C. It has a floral odor...

. This type of cleavable detergent is inherently compatible with MALDI and does not have to be removed prior to analysis:

UV light- or fluoride

Fluoride

Fluoride is the anion F−, the reduced form of fluorine when as an ion and when bonded to another element. Both organofluorine compounds and inorganic fluorine containing compounds are called fluorides. Fluoride, like other halides, is a monovalent ion . Its compounds often have properties that are...

-cleavable surfactants have also been developed but are not in current use.