Degradation of α-pinene oxide and [²H₇]-2,5,6- trimethyl-hept-(2E)-enoic acid by Pseudomonas fluorescens NCIMB 11761

verfasst von

H. Zorn, F. Neuser, R. G. Berger

Abstract

When submerged cultured Pseudomonas fluorescens NCIMB 11761 was fed-batch supplemented with α-pinene oxide, a rapid formation of 2,6-dimethyl-5-methylene-hept-(2Z)-enal (I) (isonovalal) was observed. Biotransformation and isomerisation of (I) to the (2E)-isomer (II) (novalal) were enhanced by Lewatit OC 1064, a macroporous polystyrene adsorbent. Accelerated isomerisation in the presence of an amino donor (glycine) at pH 7.3 pointed to a merely chemical mechanism. A maximum yield of 48g of aldehydesl^-1 was achieved, but quantitative analysis of the volatile fraction showed that the molar conversion of the pinene oxide substrate reached no more than 67%. To fill this gap of the mass balance, the acidic fraction was isolated. It contained several compounds which suggested a β-oxidation- like catabolism starting from 2,6-dimethyl-5-methylene-hept-(2E)-enoic acid (III) (novalic acid). Using [²H₇]-2,5,6-dimethyl-hept-(2E) -enoic acid as a conversion substrate and gas chromatography coupled to atomic emission detection and mass spectrometry a degradation pathway via labelled 3,4-dimethylpentenoic and methylpropanoic acids was evidenced. This pathway may play a predominant role in isoprenoid degradation by soil bacteria.

Organisationseinheit(en)

Institut für Lebensmittelchemie

Typ

Artikel

Journal

Journal of biotechnology

Band

107

Seiten

255-263

Anzahl der Seiten

9

ISSN

0168-1656

Publikationsdatum

13.12.2003

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Biotechnologie, Bioengineering, Angewandte Mikrobiologie und Biotechnologie

Elektronische Version(en)

https://doi.org/10.1016/j.jbiotec.2003.10.002 (Zugang: Unbekannt)