Strecker synthesis of amino acids:
Aldehyde and ketone are the functional groups that react to form the imine intermediate in the Strecker synthesis of amino acids.
Method of Strecker synthesis:
A method for synthesizing amino acids by the reaction of an aldehyde with ammonia in the presence of potassium cyanide is known as the Strecker amino acid synthesis. α-aminonitrile is produced by the condensation reaction, and this α-aminonitrile is then hydrolyzed to produce the required amino acid. The technique is applied commercially to make racemic methionine from methional.
Although primary and secondary amines also produce substituted amino acids, using ammonium salts only produces unsubstituted amino acids. Similar to this, using ketones in place of aldehydes results in amino acids that are α,α-disubstituted.
Reaction mechanism:
An aldehyde's carbonyl oxygen is protonated in the first phase of the reaction, which is followed by an ammonia nucleophilic attack on the carbonyl carbon. Water is separated from the intermediate iminium ion after a second proton exchange. The iminium carbon is then attacked by a cyanide ion, resulting in an aminonitrile.
The aminonitrile's nitrile nitrogen is protonated in the second step of the Strecker Synthesis, and a water molecule attacks the nitrile carbon. Proton exchange and a nucleophilic attack of water on the former nitrile carbon are followed by the formation of a 1,2-diamino-diol. The protonation of the amino group is then followed by the elimination of ammonia, and eventually, the deprotonation of a hydroxyl group results in the production of amino acids.
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