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CHAPS Detergent
CHAPS is a zwitterionic surfactant used in the laboratory to solubilize biological macromolecules such as proteins. It may be synthesized from cholic acid and is zwitterionic due to its quaternary ammonium and sulfonate groups; it is structurally similar to certain bile acids, such as taurodeoxycholic acid and taurochenodeoxycholic acid. It is used as a non- denaturing detergent in the process of protein purification and is especially useful in purifying membrane proteins, which are often sparingly soluble or insoluble in aqueous solution due to their native hydrophobicity. CHAPS is an abbreviation for 3- 3-cholamidopropyl)dimethylammonio1-propanesulfonate. A related detergent, called CHAPSO, has the same basic chemical structure with an additional hydroxyl functional group; its full chemical name is 3- 3-cholamidopropyl)dimethylammonio2-hydroxy-1-propanesulfonate. Both detergents have low light absorbance in the ultraviolet region of the electromagnetic spectrum, which is useful f ...
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Zwitterion
In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium will be established between the "parent" molecule and the zwitterion. Betaines are zwitterions that cannot isomerize to an all-neutral form, such as when the positive charge is located on a quaternary ammonium group. Similarly, a molecule containing a phosphonium group and a carboxylate group cannot isomerize. Amino acids The equilibrium is established in two stages. In the first stage, a proton is transferred from the carboxyl group to a water molecule: :H2N(R)CO2H + H2O H2N(R)CO2- + H3O+ In the second stage, a proton is transferred from the hydronium ion to the amine group: :H2N(R)CO2- + H3O+ H3N+ (R)CO2- + H2O Overall, the reaction is an isomerization reaction :H2N(R)CO2H H3N+ (R)CO2- The ratio of the concentrations of the two spec ...
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Hydrophobic
In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thus, prefer other neutral molecules and nonpolar solvents. Because water molecules are polar, hydrophobes do not dissolve well among them. Hydrophobic molecules in water often cluster together, forming micelles. Water on hydrophobic surfaces will exhibit a high contact angle. Examples of hydrophobic molecules include the alkanes, oils, fats, and greasy substances in general. Hydrophobic materials are used for oil removal from water, the management of oil spills, and chemical separation processes to remove non-polar substances from polar compounds. Hydrophobic is often used interchangeably with lipophilic, "fat-loving". However, the two terms are not synonymous. While hydrophobic substances are usually lipophilic, there are exceptions, suc ...
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Steroids
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. '' ...
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Taurochenodeoxycholic Acid
Taurochenodeoxycholic acid is a bile acid formed in the liver of most species, including humans, by conjugation of chenodeoxycholic acid with taurine. It is secreted into bile and then into intestine. It is usually ionized at physiologic pH, although it can be crystallized as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed by active transport in the terminal ileum. It is used as a cholagogue and choleretic. See also * Tauroursodeoxycholic acid, an epimer * See article about Taurodeoxycholic acid as an interferent in Perfluorooctanesulfonic acid Perfluorooctanesulfonic acid (PFOS) (conjugate base perfluorooctanesulfonate) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man-ma ... (PFOS) mass spectrometry analysis. References Bile acids Sulfonic acids Carboxamides Diols Cholanes {{steroid-stub ...
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Taurodeoxycholic Acid
Taurodeoxycholic acid is a bile acid. This compound is a closely related isomer of Taurochenodeoxycholic acid and Tauroursodeoxycholic acid sharing the exact molecular formula and molecular weight. Mass Spectrometry Interference with PFOS Benskin and colleagues (https://pubs.acs.org/doi/pdf/10.1021/ac070802d) published in 2007 an article identifying Taurodeoxycholic acid and isomers as mass spectrometry interferents with PFOS (Perfluorooctanesulfonic acid) as the two compounds share the m/z transition of 498-80. The molecular weight of PFOS and taurodeoxycholic acid and isomers are similar enough in molecular weight that most low resolution Triple quadrupole mass spectrometer are unable to distinguish these two chemicals from each other. Additionally both compounds share a Sulfonate group (leading to the ''m/z'' 80 loss) in the common mass spectrometry transition. Reiner and colleagues https://pubs.acs.org/doi/pdf/10.1021/es800770f found these bile acid compounds in chicken e ...
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Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ...
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Electromagnetic Spectrum
The electromagnetic spectrum is the range of frequencies (the spectrum) of electromagnetic radiation and their respective wavelengths and photon energies. The electromagnetic spectrum covers electromagnetic waves with frequencies ranging from below one hertz to above 1025 hertz, corresponding to wavelengths from thousands of kilometers down to a fraction of the size of an atomic nucleus. This frequency range is divided into separate bands, and the electromagnetic waves within each frequency band are called by different names; beginning at the low frequency (long wavelength) end of the spectrum these are: radio waves, microwaves, infrared, visible light, ultraviolet, X-rays, and gamma rays at the high-frequency (short wavelength) end. The electromagnetic waves in each of these bands have different characteristics, such as how they are produced, how they interact with matter, and their practical applications. There is no known limit for long and short wavelengths. Extreme ultr ...
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Ultraviolet
Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight, and constitutes about 10% of the total electromagnetic radiation output from the Sun. It is also produced by electric arcs and specialized lights, such as mercury-vapor lamps, tanning lamps, and black lights. Although long-wavelength ultraviolet is not considered an ionizing radiation because its photons lack the energy to ionization, ionize atoms, it can cause chemical reactions and causes many substances to glow or fluorescence, fluoresce. Consequently, the chemical and biological effects of UV are greater than simple heating effects, and many practical applications of UV radiation derive from its interactions with organic molecules. Short-wave ultraviolet light damages DNA and sterilizes surf ...
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Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Fun ...
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Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this f ...
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