Biocatalytic Enantioselective Hydroaminations Enabling Synthesis of N-Arylalkyl-Substituted L-Aspartic Acids

Mohammad M. Abidin, S Thangavelu*, Laura Bothof, Pieter Tepper, Andy-mark Thunnissen, Gerrit J. Poelarends*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)
46 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)6407–6411
Number of pages12
JournalOrganic & Biomolecular Chemistry
Volume19
Issue number29
Early online date30-Jun-2021
DOIs
Publication statusPublished - Aug-2021

Cite this