Work

Synthesis of Substituted Acyclic and Cyclic N‐Alkylhydrazines by Enzymatic Reductive Hydrazinations

Year: 2024

Type: article

Abstract: Imine reductases (IREDs) provide promising opportunities for the synthesis of various chiral amines. Initially, asymmetric imine reduction was reported, followed by reductive aminations of aldehydes and ketones via imines. Herein we present the reductive amination of structurally diverse carbonyls and dicarbonyls with hydrazines (reductive hydrazination), catalyzed by the IRED from Myxococcus stipitatus. In analogy to IRED‐catalyzed reductive aminations, various carbonyls and dicarbonyls could react with simple hydrazines to produce substituted acyclic and cyclic N‐alkylhydrazines. By incorporating and scaling up a hydrogenase cofactor regeneration system, we demonstrated the scalability and atom‐efficiency of an H2‐driven double reductive hydrazination, highlightling the potential of IREDs in biocatalysis.

Source: ChemBioChem

DOI: 10.1002/cbic.202400700

Authors: Niels Borlinghaus, Donato Calabrese, Lars Lauterbach, Bettina M. Nestl

Institutions: University of Stuttgart, RWTH Aachen University

Language: English

Topic: Enzyme Catalysis and Immobilization

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,220

Funders: European Commission, Deutsche Forschungsgemeinschaft