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Biocatalytic enantioselective hydroaminations enabling synthesis of N-arylalkyl-substituted L-aspartic acids.

ABSTRACT: N-Substituted l-aspartic acids are important chiral building blocks for pharmaceuticals and food additives. Here we report the asymmetric synthesis of various N-arylalkyl-substituted l-aspartic acids using ethylenediamine-N,N'-disuccinic acid lyase (EDDS lyase) as a biocatalyst. This C-N lyase shows a broad non-natural amine substrate scope and outstanding enantioselectivity, allowing the efficient addition of structurally diverse arylalkylamines to fumarate to afford the corresponding N-arylalkyl-substituted l-aspartic acids in good isolated yield (up to 79%) and with excellent enantiopurity (>99% ee). These results further demonstrate that C-N lyases working in reverse constitute an extremely powerful synthetic tool to prepare difficult noncanonical amino acids.

SUBMITTER: Abidin MZ

PROVIDER: S-EPMC8317194 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Biocatalytic enantioselective hydroaminations enabling synthesis of <i>N</i>-arylalkyl-substituted L-aspartic acids.

Abidin Mohammad Z MZ Saravanan Thangavelu T Bothof Laura L Tepper Pieter G PG Thunnissen Andy-Mark W H AWH Poelarends Gerrit J GJ

Organic & biomolecular chemistry 20210701 29

N-Substituted l-aspartic acids are important chiral building blocks for pharmaceuticals and food additives. Here we report the asymmetric synthesis of various N-arylalkyl-substituted l-aspartic acids using ethylenediamine-N,N'-disuccinic acid lyase (EDDS lyase) as a biocatalyst. This C-N lyase shows a broad non-natural amine substrate scope and outstanding enantioselectivity, allowing the efficient addition of structurally diverse arylalkylamines to fumarate to afford the corresponding N-arylalk ...[more]

PMID: 34235532

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