Shiina Macrolactonization
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Shiina Macrolactonization
Shiina macrolactonization (or Shiina lactonization) is an organic chemical reaction that synthesizes cyclic compounds by using aromatic carboxylic acid anhydrides as dehydration condensation agents. In 1994, Prof. Isamu Shiina (Tokyo University of Science, Japan) reported an acidic cyclization method using Lewis acid catalyst, and, in 2002, a basic cyclization using nucleophilic catalyst. Mechanism The slow addition of hydroxycarboxylic acids (seco acids) into a system containing aromatic carboxylic acid anhydride and catalyst produces corresponding lactones (cyclic esters) through the process shown in the following figure. In acidic Shiina macrolactonization, Lewis acid catalysts are used, while nucleophilic catalysts are used for Shiina macrolactonization under basic conditions. In the acidic reaction, 4-trifluoromethylbenzoic anhydride (TFBA) is mainly used as a dehydration condensation agent. First, the Lewis acid catalyst activates the TFBA, and then a carboxyl group in se ...
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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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Deprotonation
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu/hjakubowski/classes/ch331/protstructure/PS_2A3_AA_Charges.html, accessed 12/2/2020 The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is the conjugate acid of that base. A species that can either accept or donate a proton is referred to as amphiprotic. An example is the H2O (water) molecule, which can gain a proton to form the hydronium ion, H3O+, or lose a proton, leaving the hydroxide ion, OH−. The relative ability of a molecule to give up a proton is measured by its p''K''a value. A low p''K''a value indicates that the compound is acidic and will easily give up its proton to a base ...
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Peptide
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 pep ...
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Amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. A ...
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Bull
A bull is an intact (i.e., not castrated) adult male of the species ''Bos taurus'' (cattle). More muscular and aggressive than the females of the same species (i.e., cows), bulls have long been an important symbol in many religions, including for sacrifices. These animals play a significant role in beef ranching, dairy farming, and a variety of sporting and cultural activities, including bullfighting and bull riding. Due to their temperament, handling requires precautions. Nomenclature The female counterpart to a bull is a cow, while a male of the species that has been castrated is a ''steer'', '' ox'', or ''bullock'', although in North America, this last term refers to a young bull. Use of these terms varies considerably with area and dialect. Colloquially, people unfamiliar with cattle may refer to both castrated and intact animals as "bulls". A wild, young, unmarked bull is known as a ''micky'' in Australia.Sheena Coupe (ed.), ''Frontier Country, Vol. 1'' (Weldon R ...
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Pharmaceutical Drug
A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and relies on the science of pharmacology for continual advancement and on pharmacy for appropriate management. Drugs are classified in multiple ways. One of the key divisions is by level of control, which distinguishes prescription drugs (those that a pharmacist dispenses only on the order of a physician, physician assistant, or qualified nurse) from over-the-counter drugs (those that consumers can order for themselves). Another key distinction is between traditional small molecule drugs, usually derived from chemical synthesis, and biopharmaceuticals, which include recombinant proteins, vaccines, blood products used therapeutically (such as IVIG), gene therapy, monoclonal antibodies and cell therapy (for instance, stem cell therapies) ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabolites ...
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Shiina Esterification
Shiina esterification is an organic chemical reaction that synthesizes carboxylic esters from nearly equal amounts of carboxylic acids and alcohols by using aromatic carboxylic acid anhydrides as Dehydration reaction, dehydration condensation agents. In 1994, Prof. Isamu Shiina (Tokyo University of Science, Japan) reported an acidic coupling method using Lewis acid, and, in 2002, a basic esterification using nucleophilic catalyst. Mechanism The successive addition of carboxylic acids and alcohols into a system containing aromatic carboxylic acid anhydride and catalyst produces corresponding carboxylic esters through the process shown in the following figure. In acidic Shiina esterification, Lewis acid catalysts are used, while nucleophilic catalysts are used for Shiina esterification under basic conditions. In the acidic reaction, 4-trifluoromethylbenzoic anhydride (TFBA) is mainly used as a dehydration condensation agent. First, the Lewis acid catalyst activates the TFBA, and th ...
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Intermolecular Force
An intermolecular force (IMF) (or secondary force) is the force that mediates interaction between molecules, including the electromagnetic forces of attraction or repulsion which act between atoms and other types of neighbouring particles, e.g. atoms or ions. Intermolecular forces are weak relative to intramolecular forces – the forces which hold a molecule together. For example, the covalent bond, involving sharing electron pairs between atoms, is much stronger than the forces present between neighboring molecules. Both sets of forces are essential parts of force fields frequently used in molecular mechanics. The investigation of intermolecular forces starts from macroscopic observations which indicate the existence and action of forces at a molecular level. These observations include non-ideal-gas thermodynamic behavior reflected by virial coefficients, vapor pressure, viscosity, superficial tension, and absorption data. The first reference to the nature of microscopic forc ...
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Intramolecular Reaction
Intramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Examples * intramolecular hydride transfer (transfer of a hydride ion from one part to another within the same molecule) * intramolecular hydrogen bond (a hydrogen bond formed between two functional groups of the same molecule) *cyclization of ω-haloalkylamines and alcohols to form the corresponding saturated nitrogen and oxygen heterocycles, respectively (an SN2 reaction within the same molecule) In intramolecular organic reactions, two reaction sites are contained within a single molecule. This creates a very high effective concentration (resulting in high reaction rates), and, therefore, many intramolecular reactions that would not occur as an intermolecular reaction between two compounds take place. Examples of intramolecular reactions are the Smiles rearrangement, the Dieckmann condensation ...
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Syringe Driver
A syringe driver, also known as a syringe pump, is a small infusion pump, used to gradually administer small amounts of fluid (with or without medication) to a patient or for use in chemical and biomedical research. Some syringe drivers can both infuse and withdraw solutions. Uses Syringe drivers can be used for electrospinning, electrospraying, microdialysis, microfluidics, dispensing/dilution, tissue perfusion, and fluid circulation. Intravenous therapy Syringe drivers are useful for delivering intravenous (IV) therapies over several minutes. They infuse solutions at a constant rate. In the case of a medication which should be slowly pushed in over the course of several minutes, this device saves staff time and reduces medical errors. It is useful for patients who cannot take medicines orally (such as those with difficulty swallowing), and for medications too harmful to be taken orally. Palliative care Syringe drivers are particularly useful in palliative care, to con ...
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