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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 is typically very slow, but it can be accelerated with Lewis acid [1] and organometallic catalysts. [2] Primary amides (RC(O)NH 2) are more amenable to this reaction.
Transamination is mediated by several types of aminotransferase enzymes. An aminotransferase may be specific for an individual amino acid, or it may be able to process any member of a group of similar ones, for example the branched-chain amino acids, which comprises valine, isoleucine, and leucine.
In organic chemistry, transamidification is the process of exchanging the subunits of a peptide, amide or ester compound with another amine or fatty acid to produce a new amide or peptide. The process has been used for the production of emulsifiers and dispersing agents [ 1 ] and oil drilling fluids.
The upper reaction shows how a transaminase combines with a glutamine residue, releasing ammonia, and then the combination reacts with the amine group of a lysine residue of another protein, setting the enzyme free again. Nine transglutaminases have been characterised in humans, [5] eight of which catalyse transamidation reactions.
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. [1] [2] The rearrangement has also been successfully performed on haloimines and nitrones.
Created Date: 8/30/2012 4:52:52 PM
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The mechanism commonly ascribed to SHMT enzymatic activity is a transamidation followed by a cleavage of amino acid side chain from the backbone. [7] The N-terminal amine of serine makes a nucleophilic attack on the aldimine between the SHMT lysine (Internal Aldimine) and the PLP aldehyde to form a gem-diamine, and then the N-terminal amine lone pair comes down to displace the lysine, forming ...