Engineered C–N Lyase: Enantioselective Synthesis of Chiral Synthons for Artificial Dipeptide Sweeteners
Abstract: Aspartic acid derivatives with branched N‐alkyl or N‐arylalkyl substituents are valuable precursors to artificial dipeptide sweeteners such as neotame and advantame. The development of a biocatalyst to synthesize these compounds in a single asymmetric step is an as yet unmet challenge. Reported here is an enantioselective biocatalytic synthesis of various difficult N‐substituted aspartic acids, including N‐(3,3‐dimethylbutyl)‐l‐aspartic acid and N‐[3‐(3‐hydroxy‐4‐methoxyphenyl) propyl]‐l‐aspartic acid, precursors to neotame and advantame, respectively, using an engineered variant of ethylenediamine‐N,N′‐disuccinic acid (EDDS) lyase from Chelativorans sp. BNC1. This engineered C–N lyase (mutant D290M/Y320M) displayed a remarkable 1140‐fold increase in activity for the selective hydroamination of fumarate compared to that of the wild‐type enzyme. These results present new opportunities to develop practical multienzymatic processes for the more sustainable and step‐economic synthesis of an important class of food additives.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Engineered C–N Lyase: Enantioselective Synthesis of Chiral Synthons for Artificial Dipeptide Sweeteners ; volume:132 ; number:1 ; year:2020 ; pages:437-443 ; extent:7
Angewandte Chemie ; 132, Heft 1 (2020), 437-443 (gesamt 7)
- Creator
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Zhang, Jielin
Grandi, Eleonora
Fu, Haigen
Saravanan, Thangavelu
Bothof, Laura
Tepper, Pieter G.
Thunnissen, Andy‐Mark W. H.
Poelarends, Gerrit
- DOI
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10.1002/ange.201910704
- URN
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urn:nbn:de:101:1-2022052511204265899126
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:31 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Zhang, Jielin
- Grandi, Eleonora
- Fu, Haigen
- Saravanan, Thangavelu
- Bothof, Laura
- Tepper, Pieter G.
- Thunnissen, Andy‐Mark W. H.
- Poelarends, Gerrit
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Chiral resorcinarenes as enantioselective receptors
Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres
Chiral γ-Lactams by Enantioselective Cyclopropane Functionalization
Chiral Metallopolymers for Redox‐Mediated Enantioselective Interactions
Enantioselective Synthesis of Planar Chiral Ferrocene Triflones
Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction
The potential of chiral solvents in enantioselective crystallization
Enantioselective Electrochemical Lactonization Using Chiral Iodoarenes as Mediators
Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls
Enantioselective Friedel-Crafts Alkylations by Strained Chiral Silacycle
Enantioselective adsorption on chiral ceramics with medium entropy
Engineered C–N Lyase: Enantioselective Synthesis of Chiral Synthons for Artificial Dipeptide Sweeteners
Chiral resorcinarenes as enantioselective receptors
Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres
Chiral γ-Lactams by Enantioselective Cyclopropane Functionalization
Chiral Metallopolymers for Redox‐Mediated Enantioselective Interactions
Enantioselective Synthesis of Planar Chiral Ferrocene Triflones
Engineered Biocatalyst Permits Enantioselective Morita–Baylis–Hillman Reaction
The potential of chiral solvents in enantioselective crystallization
Enantioselective Electrochemical Lactonization Using Chiral Iodoarenes as Mediators
Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls
Enantioselective Friedel-Crafts Alkylations by Strained Chiral Silacycle