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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Scalable and sustainable synthesis of chiral amines by biocatalysis

Matthew J Takle1,2, David M Maurer3, Philipp Staehle3

  • 1Department of Chemistry, Molecular Sciences Research Hub, Imperial College London, London, UK.

Communications Chemistry
|December 12, 2025
PubMed

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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