Details
| Original language | English |
|---|---|
| Pages (from-to) | 255-263 |
| Number of pages | 9 |
| Journal | Journal of biotechnology |
| Volume | 107 |
| Issue number | 3 |
| Publication status | Published - 13 Dec 2003 |
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.
Keywords
- Atomic emission detection, Deuterium labelling, Isoprenoid degradation, Pseudomonas fluorescens, α-Pinene, β-Oxidation
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Chemical Engineering(all)
- Bioengineering
- Immunology and Microbiology(all)
- Applied Microbiology and Biotechnology
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In: Journal of biotechnology, Vol. 107, No. 3, 13.12.2003, p. 255-263.
Research output: Contribution to journal › Article › Research › peer review
}
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 -