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Transamidation information


Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide:

RC(O)NR'2 + HNR"2 → RC(O)NR"2 + HNR'2

The reaction is typically very slow, but it can be accelerated with Lewis acid[1] and organometallic catalysts.[2] Primary amides (RC(O)NH2) are more amenable to this reaction.

  1. ^ T. A. Dineen; M. A. Zajac; A. G. Myers (2006). "Efficient Transamidation of Primary Carboxamides by in situ Activation with N,N-Dialkylformamide Dimethyl Acetals". J. Am. Chem. Soc. 128 (50): 16406–16409. doi:10.1021/ja066728i. PMID 17165798.
  2. ^ Emma L. Baker; Michael M. Yamano; Yujing Zhou; Sarah M. Anthony; Neil K. Garg (2016). "A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis". Nature Communications. 7: 11554. Bibcode:2016NatCo...711554B. doi:10.1038/ncomms11554. PMC 4876455. PMID 27199089.

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Transamidation

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Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide: RC(O)NR'2 + HNR"2 → RC(O)NR"2 + HNR'2 The reaction...

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Amide

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S2CID 43671648. T. A. Dineen; M. A. Zajac; A. G. Myers (2006). "Efficient Transamidation of Primary Carboxamides by in situ Activation with N,N-Dialkylformamide...

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Biurea

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body through excretion. Biurea is produced from urea and hydrazine by transamidation. Its major use is as a chemical intermediate in the production of azodicarbonamide...

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Amino acid

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the amino group is then fed into the urea cycle. The other product of transamidation is a keto acid that enters the citric acid cycle. Glucogenic amino acids...

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Aspartic acid

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"semialdehyde", O2CCH(NH2)CH2CHO. Asparagine is derived from aspartate via transamidation: −O2CCH(NH2)CH2CO2− + GC(O)NH3+ → O2CCH(NH2)CH2CONH3+ + GC(O)O (where...

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Nylon

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of blends to be made. The two polymers can react with one another by transamidation to form random copolymers. According to their crystallinity, polyamides...

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Coeliac disease

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effectively. These peptides are modified by tTG in two ways, deamidation or transamidation. Deamidation is the reaction by which a glutamate residue is formed...

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Tissue transglutaminase

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nucleus, and the plasma membrane. It requires calcium as a cofactor for transamidation activity. Transcription is increased by retinoic acid. Among its many...

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Transglutaminase

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transglutaminases have been characterised in humans, eight of which catalyse transamidation reactions. These TGases have a three or four-domain organization, with...

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Penicillin

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because it does not show strong antibiotic activity. The final step is a transamidation by isopenicillin N N-acyltransferase, in which the α-aminoadipyl side-chain...

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Neurodegenerative disease

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type of covalent bonds termed isopeptide bonds, in a reaction termed transamidation or crosslinking. Transglutaminase binding of these proteins and peptides...

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Ureas

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hence mostly been limited to laboratory-scale work. Urea undergoes transamidation with alkyl and aryl amines: (H2N)2CO + R2NH → (R2N)(H2N)CO + NH3 (R2N)(H2N)CO...

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Amidase

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heterotrimeric enzyme that catalyses the formation of Gln-tRNA(Gln) by the transamidation of misacylated Glu-tRNA(Gln) via amidolysis of glutamine. As of late...

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Thioureas

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thioureas: HNR2 + S=C=NR' → S=C(NR2)(NHR') Cyclic thioureas are prepared by transamidation of thiourea with diamines. Ethylene thiourea is synthesized by treating...

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Serine hydroxymethyltransferase

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transfer. The mechanism commonly ascribed to SHMT enzymatic activity is a transamidation followed by a cleavage of amino acid side chain from the backbone. The...

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Plasma membrane monoamine transporter

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PMC 5293005. PMID 27317943. Muma NA, Mi Z (July 2015). "Serotonylation and Transamidation of Other Monoamines". ACS Chemical Neuroscience. 6 (7): 961–969. doi:10...

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S100A11

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4049/jimmunol.175.12.8296. PMID 16339570. Cecil DL, Terkeltaub R (June 2008). "Transamidation by transglutaminase 2 transforms S100A11 calgranulin into a procatabolic...

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Sequence analysis of synthetic polymers

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beginning of a transreaction process (e. g. transesterification or transamidation), the degree of randomness χ ≈ 0 as the system comprises a physical...

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QARS

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mitochondria, and chloroplasts, in which Gln-tRNA(Gln) is formed by transamidation of the misacylated Glu-tRNA(Gln). Glutaminyl-tRNA synthetase belongs...

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