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Peptide synthesis

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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. [1]

93 relations: Acetic acid, Alpha helix, Amide, Amine, Amino acid, Amyloid, Angewandte Chemie, Aromaticity, Atom economy, Bailey peptide synthesis, Biological activity, Biological half-life, C-terminus, Carbamate, Carbodiimide, Carbon dioxide, Carboxylic acid, ChemComm, Chemical ligation, Chemische Berichte, Clicked peptide polymer, Cresol, Cyclic peptide, Depsipeptide, Dimethylformamide, Enfuvirtide, Epimer, Ester, Ethyl cyanohydroxyiminoacetate, Fluorene, Fluorenylmethyloxycarbonyl protecting group, Glutamic acid, Guanidine, HATU, HBTU, HCTU, Hexafluorophosphate, High-performance liquid chromatography, Hydrogen bromide, Hydrogen fluoride, Hydrogenation, Hydroxybenzotriazole, Intein, Journal of the American Chemical Society, Lithography, Lysine, Macrocycle, Max Bergmann, Medicon Valley, Methine group, ..., Morpholine, Multicolumn countercurrent solvent gradient purification, N,N'-Dicyclohexylcarbodiimide, N,N'-Diisopropylcarbodiimide, Native chemical ligation, Neighbouring group participation, Nucleophile, Oligomer, Oligonucleotide synthesis, Organic chemistry, Particle aggregation, Peptide, Peptide bond, Peptide synthesis, Phosphonium, Photochemistry, Piperidine, Polymerization, Protecting group, Protein biosynthesis, Protein microarray, Protein primary structure, Protein production, PyAOP reagent, PyBOP, Pyridine, Racemization, Robert Bruce Merrifield, Sortase, Tert-Butyloxycarbonyl protecting group, Tetrafluoroborate, Tetrahedron Letters, Tetrakis(triphenylphosphine)palladium(0), Triazole, Trifluoroacetic acid, Triisopropylsilane, Triphenylmethane, Urea, Work-up (chemistry), Yield (chemistry), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-Hydroxy-7-azabenzotriazole, 9-Methylene-fluorene. Expand index (43 more) »

Acetic acid

Acetic acid, systematically named ethanoic acid, is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2).

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Alpha helix

The alpha helix (α-helix) is a common motif in the secondary structure of proteins and is a righthand-spiral conformation (i.e. helix) in which every backbone N−H group donates a hydrogen bond to the backbone C.

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An amide (or or), also known as an acid amide, is a compound with the functional group RnE(O)xNR′2 (R and R′ refer to H or organic groups).

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In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair.

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Amino acid

Amino acids are organic compounds containing amine (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid.

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Amyloids are aggregates of proteins that become folded into a shape that allows many copies of that protein to stick together forming fibrils.

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Angewandte Chemie

Angewandte Chemie (meaning "Applied Chemistry") is a weekly peer-reviewed scientific journal that is published by Wiley-VCH on behalf of the German Chemical Society (Gesellschaft Deutscher Chemiker).

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In organic chemistry, the term aromaticity is used to describe a cyclic (ring-shaped), planar (flat) molecule with a ring of resonance bonds that exhibits more stability than other geometric or connective arrangements with the same set of atoms.

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Atom economy

Atom economy (atom efficiency) is the conversion efficiency of a chemical process in terms of all atoms involved and the desired products produced.

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Bailey peptide synthesis

The Bailey peptide synthesis is a name reaction in organic chemistry developed 1949 by J. L. Bailey.

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Biological activity

In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter.

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Biological half-life

The biological half-life of a biological substance is the time it takes for half to be removed by biological processes when the rate of removal is roughly exponential.

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The C-terminus (also known as the carboxyl-terminus, carboxy-terminus, C-terminal tail, C-terminal end, or COOH-terminus) is the end of an amino acid chain (protein or polypeptide), terminated by a free carboxyl group (-COOH).

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A carbamate is an organic compound derived from carbamic acid (NH2COOH).

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A carbodiimide or a methanediimine is a functional group consisting of the formula RN.

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Carbon dioxide

Carbon dioxide (chemical formula) is a colorless gas with a density about 60% higher than that of dry air.

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Carboxylic acid

A carboxylic acid is an organic compound that contains a carboxyl group (C(.

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ChemComm (or Chemical Communications), formerly known as Journal of the Chemical Society D: Chemical Communications (1969–1971), Journal of the Chemical Society, Chemical Communications (1972–1995), is a peer-reviewed scientific journal published by the Royal Society of Chemistry.

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Chemical ligation

Chemical ligation is a set of techniques used for creating long peptide or protein chains.

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Chemische Berichte

Chemische Berichte (usually abbreviated as Ber. or Chem. Ber.) was a German-language scientific journal of all disciplines of chemistry founded in 1868.

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Clicked peptide polymer

Clicked peptide polymers are poly-triazole-poly-peptide hybrid polymers.

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Cresols (also hydroxytoluene) are organic compounds which are methylphenols.

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Cyclic peptide

Cyclic peptides are polypeptide chains which contain a circular sequence of bonds.

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A depsipeptide is a peptide in which one or more of its amide, -C(O)NHR-, groups are replaced by the corresponding ester, -C(O)OR, or more generally, is a molecule that has both peptide and ester linkages in proximity in the same amino acid-containing small molecule or chain.

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Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H.

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Enfuvirtide (INN) is an HIV fusion inhibitor, the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection.

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In stereochemistry, an epimer is one of a pair of stereoisomers.

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In chemistry, an ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group.

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Ethyl cyanohydroxyiminoacetate

Ethyl cyanohydroxyiminoacetate (oxyma) is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis.

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Fluorene, or 9H-fluorene, is a polycyclic aromatic hydrocarbon.

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Fluorenylmethyloxycarbonyl protecting group

The fluorenylmethyloxycarbonyl protecting group (Fmoc) is a base-labile protecting group used in organic synthesis.

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Glutamic acid

Glutamic acid (symbol Glu or E) is an α-amino acid with formula.

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Guanidine is the compound with the formula HNC(NH2)2.

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HATU (1--1H-1,2,3-triazolopyridinium 3-oxid hexafluorophosphate, Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium) is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid.

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HBTU (2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, Hexafluorophosphate Benzotriazole Tetramethyl Uronium) is a coupling reagent used in solid phase peptide synthesis.

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HCTU is an aminium coupling reagent used in peptide synthesis.

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Hexafluorophosphate is an anion with chemical formula of.

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High-performance liquid chromatography

High-performance liquid chromatography (HPLC; formerly referred to as high-pressure liquid chromatography), is a technique in analytical chemistry used to separate, identify, and quantify each component in a mixture.

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Hydrogen bromide

Hydrogen bromide is the diatomic molecule with the formula.

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Hydrogen fluoride

Hydrogen fluoride is a chemical compound with the chemical formula.

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Hydrogenation – to treat with hydrogen – is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum.

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Hydroxybenzotriazole (abbreviated HOBt) is an organic compound that is a derivative of benzotriazole.

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An intein is a segment of a protein that is able to excise itself and join the remaining portions (the exteins) with a peptide bond in a process termed protein splicing.

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Journal of the American Chemical Society

The Journal of the American Chemical Society (also known as JACS) is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society.

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Lithography is a method of printing originally based on the immiscibility of oil and water.

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Lysine (symbol Lys or K) is an α-amino acid that is used in the biosynthesis of proteins.

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Macrocycles are often described as a molecule containing twelve or more atoms with at least one large ring.

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Max Bergmann

Max Bergmann (12 February 1886 – 7 November 1944) was a Jewish-German biochemist.

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Medicon Valley

Medicon Valley is a leading bi-national life-sciences cluster in Europe, spanning the Greater Copenhagen region of eastern Denmark and southern Sweden.

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Methine group

In chemistry, methine is a trivalent functional group.

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Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH.

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Multicolumn countercurrent solvent gradient purification

Multicolumn Countercurrent Solvent Gradient Purification (MCSGP) is a form of chromatography that is used to separate or purify biomolecules from complex mixtures.

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N,N'-Dicyclohexylcarbodiimide is an organic compound with the chemical formula C13H22N2 whose primary use is to couple amino acids during artificial peptide synthesis.

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N,N′-Diisopropylcarbodiimide is a carbodiimide used in peptide synthesis.

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Native chemical ligation

Native chemical ligation or NCL is an important extension of the chemical ligation field, a concept for constructing a large polypeptide formed by the assembling of two or more unprotected peptides segments.

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Neighbouring group participation

Neighbouring group participation (NGP) (also known as anchimeric assistance) in organic chemistry has been defined by IUPAC as the interaction of a reaction centre with a lone pair of electrons in an atom or the electrons present in a sigma bond or pi bond contained within the parent molecule but not conjugated with the reaction centre.

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Nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction.

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An oligomer (oligo-, "a few" + -mer, "parts") is a molecular complex of chemicals that consists of a few monomer units, in contrast to a polymer, where the number of monomers is, in principle, infinite.

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Oligonucleotide synthesis

Oligonucleotide synthesis is the chemical synthesis of relatively short fragments of nucleic acids with defined chemical structure (sequence).

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Organic chemistry

Organic chemistry is a chemistry subdiscipline involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.

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Particle aggregation

Particle agglomeration refers to formation of assemblages in a suspension and represents a mechanism leading to destabilization of colloidal systems.

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Peptides (from Gr.: πεπτός, peptós "digested"; derived from πέσσειν, péssein "to digest") are short chains of amino acid monomers linked by peptide (amide) bonds.

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Peptide bond

A peptide bond is a covalent chemical bond linking two consecutive amino acid monomers along a peptide or protein chain.

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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.

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The phosphonium (more obscurely: phosphinium) cation describes polyatomic cations with the chemical formula.

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Photochemistry is the branch of chemistry concerned with the chemical effects of light.

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Piperidine is an organic compound with the molecular formula (CH2)5NH.

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In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks.

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Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction.

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Protein biosynthesis

Protein synthesis is the process whereby biological cells generate new proteins; it is balanced by the loss of cellular proteins via degradation or export.

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Protein microarray

A protein microarray (or protein chip) is a high-throughput method used to track the interactions and activities of proteins, and to determine their function, and determining function on a large scale.

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Protein primary structure

Protein primary structure is the linear sequence of amino acids in a peptide or protein.

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Protein production

Protein production is the biotechnological process of generating a specific protein.

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PyAOP reagent

PyAOP ((7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) is a coupling reagent used in solid phase peptide synthesis.

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PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) is a peptide coupling reagent used in solid phase peptide synthesis.

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Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N.

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In chemistry, racemization is the conversion of an enantiomerically pure mixture (one where only one enantiomer is present) into a mixture where more than one of the enantiomers are present.

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Robert Bruce Merrifield

Robert Bruce Merrifield (July 15, 1921 – May 14, 2006) was an American biochemist who won the Nobel Prize in Chemistry in 1984 for the invention of solid phase peptide synthesis.

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Sortase refers to a group of prokaryotic enzymes that modify surface proteins by recognizing and cleaving a carboxyl-terminal sorting signal.

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Tert-Butyloxycarbonyl protecting group

The tert-butyloxycarbonyl protecting group (BOC group) is a protecting group used in organic synthesis.

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Tetrafluoroborate is the anion BF4−.

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Tetrahedron Letters

Tetrahedron Letters is a weekly international journal for rapid publication of full original research papers in the field of organic chemistry.

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Tetrakis(triphenylphosphine)palladium(0) (sometimes called quatrotriphenylphosphine) is the chemical compound Pd4, often abbreviated Pd(PPh3)4, or rarely PdP4.

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A triazole refers to any of the heterocyclic compounds with molecular formula C2H3N3, having a five-membered ring of two carbon atoms and three nitrogen atoms.

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Trifluoroacetic acid

Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H.

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Triisopropyl silane (TIPS) is a organosilicon compound with the formula (i-Pr)3SiH ((i-Pr.

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Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH.

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Urea, also known as carbamide, is an organic compound with chemical formula CO(NH2)2.

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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.

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Yield (chemistry)

In chemistry, yield, also referred to as reaction yield, is the amount of product obtained in a chemical reaction.

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1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, EDAC or EDCI) is a water-soluble carbodiimide usually obtained as the hydrochloride.

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1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole used as a peptide coupling reagent.

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9-Methylene-fluorene or Dibenzofulvene(DMF) is a polycyclic aromatic hydrocarbon with chemical formula C14H10.

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[1] https://en.wikipedia.org/wiki/Peptide_synthesis

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