PMID- 10103229 OWN - NLM STAT- MEDLINE DCOM- 19991005 LR - 20240322 IS - 0099-2240 (Print) IS - 1098-5336 (Electronic) IS - 0099-2240 (Linking) VI - 65 IP - 4 DP - 1999 Apr TI - Initial reactions in the biodegradation of 1-chloro-4-nitrobenzene by a newly isolated bacterium, strain LW1. PG - 1405-12 AB - Bacterial strain LW1, which belongs to the family Comamonadaceae, utilizes 1-chloro-4-nitrobenzene (1C4NB) as a sole source of carbon, nitrogen, and energy. Suspensions of 1C4NB-grown cells removed 1C4NB from culture fluids, and there was a concomitant release of ammonia and chloride. Under anaerobic conditions LW1 transformed 1C4NB into a product which was identified as 2-amino-5-chlorophenol by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. This transformation indicated that there was partial reduction of the nitro group to the hydroxylamino substituent, followed by Bamberger rearrangement. In the presence of oxygen but in the absence of NAD, fast transformation of 2-amino-5-chlorophenol into a transiently stable yellow product was observed with resting cells and cell extracts. This compound exhibited an absorption maximum at 395 nm and was further converted to a dead-end product with maxima at 226 and 272 nm. The compound formed was subsequently identified by 1H and 13C NMR spectroscopy and mass spectrometry as 5-chloropicolinic acid. In contrast, when NAD was added in the presence of oxygen, only minor amounts of 5-chloropicolinic acid were formed, and a new product, which exhibited an absorption maximum at 306 nm, accumulated. FAU - Katsivela, E AU - Katsivela E AD - Division of Microbiology, GBF-National Research Centre for Biotechnology, D-38124 Braunschweig, Germany. EKA@gbf.de FAU - Wray, V AU - Wray V FAU - Pieper, D H AU - Pieper DH FAU - Wittich, R M AU - Wittich RM LA - eng SI - GENBANK/AJ130765 PT - Journal Article PT - Research Support, Non-U.S. Gov't PL - United States TA - Appl Environ Microbiol JT - Applied and environmental microbiology JID - 7605801 RN - 0 (Chlorophenols) RN - 0 (Culture Media) RN - 0 (Nitrobenzenes) RN - 0 (RNA, Ribosomal, 16S) RN - 28443-50-7 (2-amino-5-chlorophenol) RN - CVL66U249D (4-chloronitrobenzene) RN - EC 1.13.- (Oxygenases) SB - IM MH - Aerobiosis MH - Anaerobiosis MH - Bacteria/classification/*growth & development/*metabolism MH - Biodegradation, Environmental MH - Chlorophenols/metabolism MH - Culture Media MH - Magnetic Resonance Spectroscopy MH - Molecular Sequence Data MH - Nitrobenzenes/*metabolism MH - Oxygenases/metabolism MH - RNA, Ribosomal, 16S/genetics PMC - PMC91199 EDAT- 1999/04/02 00:00 MHDA- 1999/04/02 00:01 PMCR- 1999/04/01 CRDT- 1999/04/02 00:00 PHST- 1999/04/02 00:00 [pubmed] PHST- 1999/04/02 00:01 [medline] PHST- 1999/04/02 00:00 [entrez] PHST- 1999/04/01 00:00 [pmc-release] AID - 1427 [pii] AID - 10.1128/AEM.65.4.1405-1412.1999 [doi] PST - ppublish SO - Appl Environ Microbiol. 1999 Apr;65(4):1405-12. doi: 10.1128/AEM.65.4.1405-1412.1999.