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Biocatalytic conversion of cycloalkanes to lactones using an in‐vivo cascade in Pseudomonas taiwanensis VLB120

Chemical synthesis of lactones from cycloalkanes is a multi‐step process challenged by limitations in reaction efficiency (conversion and yield), atom economy (by‐products) and environmental performance. A heterologous pathway comprising novel enzymes with compatible kinetics was designed in Pseudomonas taiwanensis VLB120 enabling in‐vivo cascade for synthesizing lactones from cycloalkanes. The respective pathway included cytochrome P450 monooxygenase (CHX), cyclohexanol dehydrogenase (CDH), and cyclohexanone monooxygenase (CHXON) from Acidovorax sp. CHX100. Resting (non‐growing) cells of the recombinant host P. taiwanensis VLB120 converted cyclohexane, cyclohexanol, and cyclohexanone to ϵ‐caprolactone at 22, 80–100, and 170 U gCDW−1, respectively. Cyclohexane (5 mM) was completely converted with a selectivity of 65% for ϵ‐caprolactone formation in 2 hr without accumulation of intermediate products. Promiscuity of the whole‐cell biocatalyst gave access to analogous lactones from cyclooctane and cyclodecane. A total product concentration of 2.3 g L−1 and a total turnover number of 36,720 was achieved over 5 hr with a biocatalyst concentration of 6.8 gCDW L−1.