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S-Nitrosothiol
In organic chemistry, ''S''-nitrosothiols, also known as thionitrites, are organic compounds or functional groups containing a nitroso group attached to the sulfur atom of a thiol. ''S''-Nitrosothiols have the general formula , where ''R'' denotes an organic group. Originally suggested by Ignarro to serve as intermediates in the action of organic nitrates, endogenous S-nitrosothiols were discovered by Stamler and colleagues (S-nitrosoalbumin in plasma and S-nitrosoglutathione in airway lining fluid) and shown to represent a main source of NO bioactivity ''in vivo''. More recently, S-nitrosothiols have been implicated as primary mediators of protein S-nitrosylation, the oxidative modification of cysteine thiol that provides ubiquitous regulation of protein function. S-Nitrosothiols have received much attention in biochemistry because they serve as donors of both the nitrosonium ion and of nitric oxide and thus best rationalize the chemistry of NO-based signaling in living ...
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S-Nitroso-N-acetylpenicillamine
''S''-Nitroso-''N''-acetylpenicillamine (SNAP) is the organosulfur compound with the formula ON S C( CH3)2 C H( N H Ac) CO2H. It is a green solid. SNAP is an ''S''-nitrosothiol and is used as a model for the general class of ''S''-nitrosothiols which have received much attention in biochemistry because nitric oxide and some organic nitroso derivatives serve as signaling molecules in living systems, especially related to vasodilation. SNAP is derived from the amino acid penicillamine Penicillamine, sold under the brand name of Cuprimine among others, is a medication primarily used for the treatment of Wilson's disease. It is also used for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, .... ''S''-Nitrosoglutathione is a related agent. References {{DEFAULTSORT:Nitroso-N-acetylpenicillamine, S- Sulfur compounds Nitroso compounds Secondary amino acids Amides ...
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Nitroso Compounds
In organic chemistry, nitroso refers to a functional group in which the nitric oxide () group is attached to an organic moiety. As such, various nitroso groups can be categorized as ''C''-nitroso compounds (e.g., nitrosoalkanes; ), ''S''-nitroso compounds ( nitrosothiols; ), ''N''-nitroso compounds (e.g., nitrosamines, ), and ''O''-nitroso compounds (alkyl nitrites; ). Synthesis Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines. Ortho-nitrosophenols may be produced by the Baudisch reaction. In the Fischer–Hepp rearrangement aromatic 4-nitrosoanilines are prepared from the corresponding nitrosamines. Properties Nitrosoarenes typically participate in a monomer–dimer equilibrium. The dimers, which are often pale yellow, are often favored in the solid state, whereas the deep-green monomers are favored in dilute solution or at higher temperatures. They exist as ''cis'' and ''trans'' isomers. Due to the stability o ...
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Jonathan Stamler
Jonathan Solomon Stamler (born June 23, 1959) is an English-born American physician and scientist. He is known for his discovery of protein S-nitrosylation, the addition of a nitric oxide (NO) group to cysteine residues in proteins, as a ubiquitous cellular signal to regulate enzymatic activity and other key protein functions in bacteria, plants and animals, and particularly in transporting NO on cysteines in hemoglobin as the third gas in the respiratory cycle. Early life and education Stamler was born in Wallingford, England on June 23, 1959 to a British father and American mother, and lived in multiple countries (United Kingdom, Switzerland, Israel, United States) as a youth due to his father's global career. He played on the Israeli national (under 18) tennis team. He graduated with a bachelor's degree from Brandeis University in 1981, and earned his M.D. degree from Icahn School of Medicine at Mount Sinai in 1985. His residency and fellowship training in pulmonary m ...
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S-Nitrosotriphenylmethanethiol
''S''-Nitrosotriphenylmethanethiol is the organosulfur compound with the formula (C6H5)3CSNO. It is a rare example of a nitrosothiol derivative that is robust solid at room temperature. The green compound can be produced by the reaction of triphenylmethanethiol with nitrous acid: :(C6H5)3CSH + HONO → (C6H5)3CSNO + H2O According to X-ray crystallography, ''S''-nitrosotriphenylmethanethiol features a conventional trityl Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmetha ... group appended to a bent SNO substituent. The S-N=O angle is 114°, while the S-N and N=O distances are 1.78 and 1.79 Å. Other ''S''-nitrosothiols, e.g. MeSNO and SNAP have characterized by similar structures. References {{DEFAULTSORT:Nitrosotriphenylmethanethiol, S- Nitroso compounds Sulfur compoun ...
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Nitrosation
Nitrosation is a process of converting organic compounds into nitroso derivatives, i.e. compounds containing the R-NO functionality. ''C''-Nitroso compounds ''C''-Nitroso compounds, such as nitrosobenzene, are typically prepared by oxidation of hydroxylamines: :RNHOH + → RNO + H2O ''S''-Nitroso compounds ''S''-Nitroso compounds ( ''S''-nitrosothiols) are typically prepared by condensation of a thiol and nitrous acid: :RSH + HONO → RSNO + H2O ''O''-Nitroso compounds ''O''-Nitroso compounds are similar to ''S''-nitroso compounds, but are less reactive because the oxygen atom is less nucleophilic than the sulfur atom. The formation of an alkyl nitrite from an alcohol and nitrous acid is a common example: :ROH + HONO → RONO + H2O ''N''-Nitrosamines ''N''-Nitrosamines, including the carcinogenic variety, arise from the reaction of nitrite sources with amino compounds, which can happen during the curing of meat. Typically this reaction proceeds via the attack of the nitros ...
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Red Blood Cell
Red blood cells (RBCs), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "hollow vessel", with ''-cyte'' translated as "cell" in modern usage), are the most common type of blood cell and the vertebrate's principal means of delivering oxygen (O2) to the body tissues—via blood flow through the circulatory system. RBCs take up oxygen in the lungs, or in fish the gills, and release it into tissues while squeezing through the body's capillaries. The cytoplasm of a red blood cell is rich in hemoglobin, an iron-containing biomolecule that can bind oxygen and is responsible for the red color of the cells and the blood. Each human red blood cell contains approximately 270 million hemoglobin molecules. The cell membrane is composed of proteins and lipids, and this structure provides properties essential for ...
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Nitroso
In organic chemistry, nitroso refers to a functional group in which the nitric oxide () group is attached to an organic moiety (chemistry), moiety. As such, various nitroso groups can be categorized as ''C''-nitroso compounds (e.g., nitrosoalkanes; ), ''S''-nitroso compounds (S-Nitrosothiol, nitrosothiols; ), ''N''-nitroso compounds (e.g., nitrosamines, ), and ''O''-nitroso compounds (alkyl nitrites; ). Synthesis Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines. Ortho-nitrosophenols may be produced by the Baudisch reaction. In the Fischer–Hepp rearrangement aromatic 4-nitrosoanilines are prepared from the corresponding nitrosamines. Properties Nitrosoarenes typically participate in a Dimerization (chemistry), monomer–dimer equilibrium. The dimers, which are often pale yellow, are often favored in the solid state, whereas the deep-green monomers are favored in dilute solution or at higher temperatures. They exist ...
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Thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' ( Mac OS X Leopard). because the thiolate group () bonds very stro ...
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Lone Pair
In chemistry, a lone pair refers to a pair of valence electrons that are not shared with another atom in a covalent bondIUPAC '' Gold Book'' definition''lone (electron) pair''/ref> and is sometimes called an unshared pair or non-bonding pair. Lone pairs are found in the outermost electron shell of atoms. They can be identified by using a Lewis structure. Electron pairs are therefore considered lone pairs if two electrons are paired but are not used in chemical bonding. Thus, the number of electrons in lone pairs plus the number of electrons in bonds equals the number of valence electrons around an atom. Lone pair is a concept used in valence shell electron pair repulsion theory (VSEPR theory) which explains the shapes of molecules. They are also referred to in the chemistry of Lewis acids and bases. However, not all non-bonding pairs of electrons are considered by chemists to be lone pairs. Examples are the transition metals where the non-bonding pairs do not influence mole ...
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Functional Groups
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. Funct ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Li ...
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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 chai ...
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