TY - JOUR

T1 - Degradation of α-pinene oxide and [2H7]-2,5,6- trimethyl-hept-(2E)-enoic acid by Pseudomonas fluorescens NCIMB 11761

AU - Zorn, H.

AU - Neuser, F.

AU - Berger, R. G.

N1 - Funding information: The authors are grateful to the Fonds der Chemischen Industrie, Frankfurt for financial support and to E. Latza for establishing Ps. fluorescens . The project is part of the joint initiative project “Biologisch aktive Naturstoffe, Chemische Diversität” at the University of Hannover.

PY - 2003/12/13

Y1 - 2003/12/13

N2 - 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.

AB - 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.

KW - Atomic emission detection

KW - Deuterium labelling

KW - Isoprenoid degradation

KW - Pseudomonas fluorescens

KW - α-Pinene

KW - β-Oxidation

UR - http://www.scopus.com/inward/record.url?scp=0347123159&partnerID=8YFLogxK

U2 - 10.1016/j.jbiotec.2003.10.002

DO - 10.1016/j.jbiotec.2003.10.002

M3 - Article

AN - SCOPUS:0347123159

VL - 107

SP - 255

EP - 263

JO - Journal of biotechnology

JF - Journal of biotechnology

SN - 0168-1656

IS - 3

ER -