Biotransformation of codeine to 14-OH-codeine derivatives by Rhizobium radiobacter R89-1

A Gram-negative bacterium transforming codeine 1a to 14-hydroxycodeine 1c was isolated from the sample of composted wastes of Papaver somniferum deposited in a factory producing poppy seed. Based on 16S ribosomal RNA gene phylogeny, biochemical and morphological properties, the strain was designated as Rhizobium radiobacter R89-1. The bacterium is able to transform 1a into four C-14-hydroxy derivatives of codeine. When used as a whole-cell catalyst, 100% conversion was achieved at concentration of 1a up to 6.0 g/L to 14-hydroxycodeine 1c as a single product. Biohydroxylation of codeine to C-14-hydroxy derivatives, a high tolerance of the strain to 1a and activity with morphine 2a make the biocatalyst promising for pharmaceutical applications.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Whole-cell biotransformation of codeine/morphine to C-14 hydroxylated products by Rhizobium radiobacter. ► Screening among 2000 strains and 60 microbial consortia. ► Optimization of transformation by whole cell catalyst. ► Conversion to C-14 hydroxy derivates: 100% conversion up to 6 g/L of codeine.