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4-Ketozeinoxanthin, a novel carotenoid produced in Escherichia coli through metabolic engineering using carotenogenic genes of bacterium and liverwort
- Maoka, Takashi, Takemura, Miho, Tokuda, Harukuni, Suzuki, Nobutaka, Misawa, Norihiko
- Tetrahedron letters 2014 v.55 no.49 pp. 6708-6710
- Escherichia coli, Marchantia polymorpha, Pantoea ananatis, biosynthesis, chemical reactions, chemical structure, genes, lycopene, lycopene beta-cyclase, lycopene epsilon-cyclase, metabolic engineering, mosses and liverworts, nuclear magnetic resonance spectroscopy, soil bacteria, spectral analysis
- In order to produce a novel keto-carotenoid in Escherichia coli, we introduced the marine bacterial carotenoid ketolase gene (crtW) into pathway-engineered E. coli producing carotenoids of plant origin, which carried the lycopene biosynthesis genes (crtE, crtB, and crtI) from soil bacterium Pantoea ananatis and the liverwort Marchantia polymorpha genes that encode lycopene β-cyclase (MpLCYb), lycopene ε-cyclase (MpLCYe), and β-carotenoid hydroxylase (MpBHY). A novel keto-carotenoid (1) was produced by these carotenoid biosynthesis genes in E. coli along with α-echinenone, adonirubin, and adonixanthin. The structure of 1 was determined as (3S,6′R)-3-hydroxy-β,ε-caroten-4-one based on Uv–vis, MS, ¹H NMR, and CD spectral data. This compound was named 4-ketozeinoxanthin and showed anti-tumor-promoting activity.