Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization.
Ecotoxicological assessment
Enantiomeric excess
Enantiomers
Gene expression
Lupanine
Pseudomonas putida LPK411
Quantitative real-time PCR
Journal
Microbial cell factories
ISSN: 1475-2859
Titre abrégé: Microb Cell Fact
Pays: England
ID NLM: 101139812
Informations de publication
Date de publication:
14 Mar 2020
14 Mar 2020
Historique:
received:
25
12
2019
accepted:
04
03
2020
entrez:
15
3
2020
pubmed:
15
3
2020
medline:
22
10
2020
Statut:
epublish
Résumé
Lupanine is a plant toxin contained in the wastewater of lupine bean processing industries, which could be used for semi-synthesis of various novel high added-value compounds. This paper introduces an environmental friendly process for microbial production of enantiopure lupanine. Previously isolated P. putida LPK411, R. rhodochrous LPK211 and Rhodococcus sp. LPK311, holding the capacity to utilize lupanine as single carbon source, were employed as biocatalysts for resolution of racemic lupanine. All strains achieved high enantiomeric excess (ee) of L-(-)-lupanine (> 95%), while with the use of LPK411 53% of the initial racemate content was not removed. LPK411 fed with lupanine enantiomers as single substrates achieved 92% of D-(+)-lupanine biodegradation, whereas L-(-)-lupanine was not metabolized. Monitoring the transcriptional kinetics of the luh gene in cultures supplemented with the racemate as well as each of the enantiomers supported the enantioselectivity of LPK411 for D-(+)-lupanine biotransformation, while (trans)-6-oxooctahydro-1H-quinolizine-3-carboxylic acid was detected as final biodegradation product from D-(+)-lupanine use. Ecotoxicological assessment demonstrated that lupanine enantiomers were less toxic to A. fischeri compared to the racemate exhibiting synergistic interaction. The biological chiral separation process of lupanine presented here constitutes an eco-friendly and low-cost alternative to widely used chemical methods for chiral separation.
Sections du résumé
BACKGROUND
BACKGROUND
Lupanine is a plant toxin contained in the wastewater of lupine bean processing industries, which could be used for semi-synthesis of various novel high added-value compounds. This paper introduces an environmental friendly process for microbial production of enantiopure lupanine.
RESULTS
RESULTS
Previously isolated P. putida LPK411, R. rhodochrous LPK211 and Rhodococcus sp. LPK311, holding the capacity to utilize lupanine as single carbon source, were employed as biocatalysts for resolution of racemic lupanine. All strains achieved high enantiomeric excess (ee) of L-(-)-lupanine (> 95%), while with the use of LPK411 53% of the initial racemate content was not removed. LPK411 fed with lupanine enantiomers as single substrates achieved 92% of D-(+)-lupanine biodegradation, whereas L-(-)-lupanine was not metabolized. Monitoring the transcriptional kinetics of the luh gene in cultures supplemented with the racemate as well as each of the enantiomers supported the enantioselectivity of LPK411 for D-(+)-lupanine biotransformation, while (trans)-6-oxooctahydro-1H-quinolizine-3-carboxylic acid was detected as final biodegradation product from D-(+)-lupanine use. Ecotoxicological assessment demonstrated that lupanine enantiomers were less toxic to A. fischeri compared to the racemate exhibiting synergistic interaction.
CONCLUSIONS
CONCLUSIONS
The biological chiral separation process of lupanine presented here constitutes an eco-friendly and low-cost alternative to widely used chemical methods for chiral separation.
Identifiants
pubmed: 32169079
doi: 10.1186/s12934-020-01324-1
pii: 10.1186/s12934-020-01324-1
pmc: PMC7071741
doi:
Substances chimiques
Waste Water
0
lupanine
183KU7535A
Sparteine
298897D62S
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
67Subventions
Organisme : Cyprus Research and Innovation Foundation
ID : ΚΟΙΝΑ/ΠΚΠ-WATER/0315/14
Organisme : Fundação para a Ciência e a Tecnologia
ID : WaterJPI/0001/2014
Organisme : Fundação para a Ciência e a Tecnologia
ID : WaterJPI/0002/2014
Organisme : Fundação para a Ciência e a Tecnologia
ID : WaterJPI/0003/2014
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