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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.
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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.
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.
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.
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 ...
Weinreb and Nahm originally proposed the following reaction mechanism to explain the selectivity shown in reactions of the Weinreb–Nahm amide. Their suggestion was that the tetrahedral intermediate (A below) formed as a result of nucleophilic addition by the organometallic reagent is stabilized by chelation from the methoxy group as shown. [1]
Cancer cells can be killed by increasing calcium levels through the activation of tTG transamidation activity. Preclinical trials have showed promise in using tTG inhibitors as anti-cancer therapeutic agents. [38] However, other studies [33] have noted that tTG transamidation activity could be linked to the inhibition of tumor cell invasiveness.