Coproduction of 5-Aminovalerate and δ-Valerolactam for the Synthesis of Nylon 5 From L-Lysine in Escherichia coli

Abstract

The compounds 5-aminovalerate and δ-valerolactam are important building blocks that can be used to synthesize bioplastics. The production of 5-aminovalerate and δ-valerolactam in microorganisms provides an ideal source that reduces the cost. To achieve efficient biobased coproduction of 5-aminovalerate and δ-valerolactam in Escherichia coli, a single biotransformation step from L-lysine was constructed. First, an equilibrium mixture was formed by L-lysine α-oxidase RaiP from Scomber japonicus. In addition, by adjusting the pH and H2O2 concentration, the titers of 5-aminovalerate and δ-valerolactam reached 10.24 and 1.82 g/L from 40 g/L L-lysine HCl at pH 5.0 and 10 mM H2O2, respectively. With the optimized pH value, the δ-valerolactam titer was improved to 6.88 g/L at pH 9.0 with a molar yield of 0.35 mol/mol lysine. The ratio of 5AVA and δ-valerolactam was obviously affected by pH value. The ratio of 5AVA and δ-valerolactam could be obtained in the range of 5.63:1–0.58:1 at pH 5.0–9.0 from the equilibrium mixture. As a result, the simultaneous synthesis of 5-aminovalerate and δ-valerolactam from L-lysine in Escherichia coli is highly promising. To our knowledge, this result constitutes the highest δ-valerolactam titer reported by biological methods. In summary, a commercially implied bioprocess developed for the coproduction of 5-aminovalerate and δ-valerolactam using engineered Escherichia coli.

Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers

“…In the method developed by Franssen and co-workers, the l -lysine α-oxidase was immobilized on an epoxy activated solid support to give a synthesis method with 5-aminovaleric acid yields of up to 95% . During the process, there is an equilibrium mixture, which could be influenced by pH to favor δ-valerolactam at higher pH . Furthermore, they managed to generate yields of 6.88 g/L of δ-valerolactam from 40 g/L l -lysine.…”

“…673 During the process, there is an equilibrium mixture, which could be influenced by pH to favor δvalerolactam at higher pH. 674 Furthermore, they managed to generate yields of 6.88 g/L of δ-valerolactam from 40 g/L Llysine.…”

Metabolic Engineering of Microorganisms Towards the Biomanufacturing of Non-Natural C5 and C6 Chemicals

“…The fuchsia pathway is shown in reference [21][22][23][24][25][62][63][64][65][66][67][68][69][70][71][72][73][74][75]. The orange pathway can be found in reference [26,76]. The grey pathway is highlighted in the reference [30,[77][78][79][80][81][82][83][84][85][86].…”

Mild hydrolysis of chemically stable valerolactams by a biocatalytic ATP-dependent system fueled by metaphosphate

“…Biotechnological access to δ-valerolactam is currently being investigated as an approach to accessing bio-sourced plastics. 9 However, the challenging biodegradability of this molecule may hamper its wider acceptance. To the best of our knowledge, no enzymatic approach has been identified for the mild cleavage of γ-butyrolactam and δ-valerolactam, and surprisingly, a variety of hydrolytic enzymes were shown inactive on these simple molecules.…”