Abstract
The trisubstituted enolate- and C-C bond-forming capacities of engineered carboxymethylproline synthases CMPSs are coupled with the malonyl-CoA synthetase MatB to enable stereoselective preparation of 5- and 6-membered N-heterocycles functionalised with alkyl-substituted carboxymethyl side chains, starting from achiral alkyl-substituted malonic acids and L-amino acid semialdehydes. The results illustrate the biocatalytic utility of crotonases in tandem enzyme-catalysed reactions for stereoselective synthesis.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bacterial Proteins / chemistry
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Bacterial Proteins / metabolism*
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Biocatalysis
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Coenzyme A Ligases / chemistry
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Coenzyme A Ligases / metabolism*
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Enoyl-CoA Hydratase / chemistry
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Enoyl-CoA Hydratase / metabolism*
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Lipids / chemistry*
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Models, Molecular
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Molecular Structure
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Pipecolic Acids / chemistry
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Pipecolic Acids / metabolism*
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Proline / biosynthesis*
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Proline / chemistry
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Protein Engineering*
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Stereoisomerism
Substances
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Bacterial Proteins
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Lipids
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Pipecolic Acids
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Proline
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Enoyl-CoA Hydratase
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Coenzyme A Ligases
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malonyl-CoA synthetase
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pipecolic acid