- Engineered C–N Lyase: Enantioselective Synthesis of Chiral Synthons for Artificial Dipeptide Sweeteners
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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.
- Zhang, Jielin,Grandi, Eleonora,Fu, Haigen,Saravanan, Thangavelu,Bothof, Laura,Tepper, Pieter G.,Thunnissen, Andy-Mark W. H.,Poelarends, Gerrit J.
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supporting information
p. 429 - 435
(2019/11/25)
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- Stereoselective Synthesis of 2,3-Diamino Acids. 2,3-Diamino-4-phenylbutanoic Acid
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The synthesis of (2S,3S)- and (2S,3R)-2,3-diamino-4-phenylbutanoic acid (1c and 3) from L-aspartic acid is described.The N-(phenylfluorenyl)-protected aspartic acid diesters 4 and 10 (α-tert-butyl, β-methyl), 18 (β-benzyl, α-tert-butyl), and 28 (β-benzyl,
- Dunn, Peter J.,Haener, Robert,Rapoport, Henry
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p. 5017 - 5025
(2007/10/02)
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