Stereoselective preparation of lipidated carboxymethyl-proline/pipecolic acid derivatives via coupling of engineered crotonases with an alkylmalonyl-CoA synthetaseElectronic supplementary information (ESI) available. See DOI: 10.1039/c3ob41525b

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,...

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Main Authors: Hamed, Refaat B, Henry, Luc, Gomez-Castellanos, J. Ruben, Asghar, Amina, Brem, Jürgen, Claridge, Timothy D. W, Schofield, Christopher J
Format: Article
Language:English
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Summary: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. Coupling of crotonases with alkylmalonyl-CoA forming enzymes enables one-pot stereoselective preparation of functionalised 5- and 6-membered N -heterocycles.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41525b