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Diisopropylcarbodiimide
''N'',''N′''-Diisopropylcarbodiimide is a carbodiimide used in peptide synthesis. As a liquid, it is easier to handle than the commonly used ''N'',''N′''-dicyclohexylcarbodiimide, a waxy solid. In addition, ''N'',''N′''-diisopropylurea, its byproduct in many chemical reactions, is soluble in most organic solvents A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ..., a property that facilitates work-up. Further reading * * {{organic-compound-stub Peptide coupling reagents Carbodiimides Reagents for biochemistry Biochemistry Biochemistry methods Isopropyl compounds ...
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Carbodiimide
In organic chemistry, a carbodiimide (systematic IUPAC name: methanediimine) is a functional group with the formula RN=C=NR. They are exclusively synthetic. A well known carbodiimide is dicyclohexylcarbodiimide, which is used in peptide synthesis. Dialkylcarbodiimides are stable. Some diaryl derivatives tend to convert to dimers and polymers upon standing at room temperature, though this mostly occurs with low melting point carbodiimides that are liquids at room temperature. Solid diaryl carbodiimides are more stable, but can slowly undergo hydrolysis in the presence of water over time. Structure and bonding From the perspective of bonding, carbodiimides are isoelectronic with carbon dioxide. Three principal resonance structures describe carbodiimides: :RN=C=NR ↔ RN+≡C-N−R ↔ RN−-C≡N+R The N=C=N core is relatively linear and the C-N=C angles approach 120°. In the case of C(NCHPh2)2, the central N=C=N angle is 170° and the C-N=C angles are within 1° of 126°. The ...
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Carbodiimides
In organic chemistry, a carbodiimide (systematic IUPAC name: methanediimine) is a functional group with the formula RN=C=NR. They are exclusively synthetic. A well known carbodiimide is dicyclohexylcarbodiimide, which is used in peptide synthesis. Dialkylcarbodiimides are stable. Some diaryl derivatives tend to convert to dimers and polymers upon standing at room temperature, though this mostly occurs with low melting point carbodiimides that are liquids at room temperature. Solid diaryl carbodiimides are more stable, but can slowly undergo hydrolysis in the presence of water over time. Structure and bonding From the perspective of bonding, carbodiimides are isoelectronic with carbon dioxide. Three principal resonance structures describe carbodiimides: :RN=C=NR ↔ RN+≡C-N−R ↔ RN−-C≡N+R The N=C=N core is relatively linear and the C-N=C angles approach 120°. In the case of C(NCHPh2)2, the central N=C=N angle is 170° and the C-N=C angles are within 1° of 126°. The ...
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Peptide Synthesis
In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis (long peptides) in living organisms occurs in the opposite direction. The chemical synthesis of peptides can be carried out using classical solution-phase techniques, although these have been replaced in most research and development settings by solid-phase methods (see below). Solution-phase synthesis retains its usefulness in large-scale production of peptides for industrial purposes how ...
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Dicyclohexylcarbodiimide
''N'',''N''′-Dicyclohexylcarbodiimide (DCC or DCCD) is an organic compound with the chemical formula (C6H11N)2C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis. The low melting point of this material allows it to be melted for easy handling. It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water. Structure and spectroscopy The C−N=C=N−C core of carbodiimides (N=C=N) is linear, being related to the structure of allene. The molecule has idealized C2 symmetry. The N=C=N moiety gives characteristic IR spectroscopic signature at 2117 cm−1. The 15N NMR spectrum shows a characteristic shift of 275 ppm upfield of nitric acid and the 13C NMR spectrum features a peak at about 139 ppm downfield from TMS. Preparation DCC is produced by the decarboxylation of cyclohexylisocyanate using phosphine oxides as a catalyst: :2 C6H11NCO ...
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Organic Solvents
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell. The quantity of solute that can dissolve in a specific volume of solvent varies with temperature. Major uses of solvents are in paints, paint removers, inks, and dry cleaning. Specific uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene); as paint thinners (toluene, turpentine); as nail polish removers and solvents of glue (acetone, methyl acetate, ethyl acetate); in spot removers (hexane, petrol ether); in detergents ( citrus terpenes); and in perfumes (ethanol). Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical synt ...
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Work-up (chemistry)
In chemistry, work-up refers to the series of manipulations required to isolate and purify the product(s) of a chemical reaction. Typically, these manipulations may include: * quenching a reaction to deactivate any unreacted reagents. * cooling the reaction mixture or adding an ''antisolvent'' to induce precipitation, and collecting or removing the solids by filtration, decantation, or centrifugation * removal of solvents by evaporation * separating the reaction mixture into organic and aqueous layers by liquid-liquid extraction * purification by chromatography, distillation or recrystallization For example, the Grignard reaction between phenylmagnesium bromide and carbon dioxide in the form of dry ice gives the conjugate base of benzoic acid. The desired product, benzoic acid, is obtained by the following work-up:{{cite book , title = Introduction to Organic Laboratory Techniques: A Small Scale Approach , author = Donald L. Pavia , year = 2004 , publisher = Thomson Brooks ...
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Tetrahedron Lett
''Tetrahedron Letters'' is a weekly international journal for rapid publication of full original research papers in the field of organic chemistry. According to the ''Journal Citation Reports'', the journal has a 2020 impact factor of 2.415. Indexing ''Tetrahedron Letters'' is indexed in: References See also *''Tetrahedron In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the o ...'' *'' Tetrahedron: Asymmetry'' Chemistry journals Weekly journals Publications established in 1959 Elsevier academic journals {{chem-journal-stub ...
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Peptide Coupling Reagents
Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. A polypeptide is a longer, continuous, unbranched peptide chain. Hence, peptides fall under the broad chemical classes of biological polymers and oligomers, alongside nucleic acids, oligosaccharides, polysaccharides, and others. A polypeptide that contains more than approximately 50 amino acids is known as a protein. Proteins consist of one or more polypeptides arranged in a biologically functional way, often bound to ligands such as coenzymes and cofactors, or to another protein or other macromolecule such as DNA or RNA, or to complex macromolecular assemblies. Amino acids that have been incorporated into peptides are termed residues. A water molecule is released during formation of each amide bond.. All peptides except cyclic peptides ...
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Reagents For Biochemistry
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a substance ''consumed'' in the course of a chemical reaction. ''Solvents'', though involved in the reaction mechanism, are usually not called reactants. Similarly, ''catalysts'' are not consumed by the reaction, so they are not reactants. In biochemistry, especially in connection with enzyme-catalyzed reactions, the reactants are commonly called substrates. Definitions Organic chemistry In organic chemistry, the term "reagent" denotes a chemical ingredient (a compound or mixture, typically of inorganic or small organic molecules) introduced to cause the desired transformation of an organic substance. Examples include the Collins reagent, Fenton's reagent, and Grignard reagents. Analytical chemistry In analytical chemistry, a reagen ...
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Biochemistry
Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and metabolism. Over the last decades of the 20th century, biochemistry has become successful at explaining living processes through these three disciplines. Almost all areas of the life sciences are being uncovered and developed through biochemical methodology and research. Voet (2005), p. 3. Biochemistry focuses on understanding the chemical basis which allows biological molecules to give rise to the processes that occur within living cells and between cells,Karp (2009), p. 2. in turn relating greatly to the understanding of tissues and organs, as well as organism structure and function.Miller (2012). p. 62. Biochemistry is closely related to molecular biology, which is the study of the molecular mechanisms of biological phenomena.As ...
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Biochemistry Methods
The following outline is provided as an overview of and topical guide to biochemistry: Biochemistry – study of chemical processes in living organisms, including living matter. Biochemistry governs all living organisms and living processes. Applications of biochemistry * Testing ** Ames test – salmonella bacteria is exposed to a chemical under question (a food additive, for example), and changes in the way the bacteria grows are measured. This test is useful for screening chemicals to see if they mutate the structure of DNA and by extension identifying their potential to cause cancer in humans. ** Pregnancy test – one uses a urine sample and the other a blood sample. Both detect the presence of the hormone human chorionic gonadotropin (hCG). This hormone is produced by the placenta shortly after implantation of the embryo into the uterine walls and accumulates. ** Breast cancer screening – identification of risk by testing for mutations in two genes&md ...
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