Biocatalytic Production of a Nylon 6 Precursor from Caprolactone in Continuous Flow

Journal article (2022)

Authors

Maria Romero-Fernandez University of Nottingham

C.M. Heckmann University of Nottingham

Francesca Paradisi University of Bern, University of Nottingham

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Biocatalysis Continuous flow Ε-caprolactone Enzyme cascade Nylon 6

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Published Date

2022

Language

English

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Abstract

6-Aminocaproic acid (6ACA) is a key building block and an attractive precursor of caprolactam, which is used to synthesize nylon 6, one of the most common polymers manufactured nowadays. (Bio)-production of platform chemicals from renewable feedstocks is instrumental to tackle climate change and decrease fossil fuel dependence. Here, the cell-free biosynthesis of 6ACA from 6-hydroxycaproic acid was achieved using a co-immobilized multienzyme system based on horse liver alcohol dehydrogenase, Halomonas elongata transaminase, and Lactobacillus pentosus NADH oxidase for in-situ cofactor recycling, with >90 % molar conversion (m.c.) The integration of a step to synthesize hydroxy-acid from lactone by immobilized Candida antarctica lipase B resulted in >80 % m.c. of ϵ-caprolactone to 6ACA, >20 % of δ-valerolactone to 5-aminovaleric acid, and 30 % of γ-butyrolactone to γ-aminobutyric acid in one-pot batch reactions. Two serial packed-bed reactors were set up using these biocatalysts and applied to the continuous-flow synthesis of 6ACA from ϵ-caprolactone, achieving a space-time yield of up to 3.31 g_6ACA h⁻¹ L⁻¹ with a segmented liquid/air flow for constant oxygen supply.