The link between nitrification and biotransformation of 17α-ethinylestradiol

Biological treatment processes are probably important for preventing the proliferation of steroidal compounds in the environment, and a growing number of reports suggest that nitrification may play a role in removing these chemicals from wastewater. The link between nitrification and biotransformation of 17 alpha-ethinylestradiol (EE2) was investigated using enriched cultures of autotrophic ammonia-oxidizers. Batch experiments showed that ring A of EE2 is the site of electrophilic initiating reactions, including conjugation and hydroxylation. Ring A was also cleaved before any of the other rings were broken, which is likely because the frontier electron density of the ring A carbon units is higher than those of rings B, C, or D. EE2 and NH3 were degraded in the presence of an ammonium monooxygenase (AMO) containing protein extract, and the reaction stoichiometry was consistent with a conceptual model involving a binuclear copper site located at the AMO active site. Continuous tests showed a linear relationship between nitrification and EE2 removal in enriched nitrifying cultures. Taken together, these results support the notion that EE2 biotransformation can be cometabolically mediated under operating conditions that allow for enrichment of nitrifiers.