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Title: Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization
Authors: Parmaki, Stella 
Tsipa, Argyro 
Vasquez Christodoulou, Marlen 
Gonçalves, João M J 
Hadjiadamou, Ioanna 
Ferreira, Frederico C. 
Afonso, Carlos A.M. 
Drouza, Chryssoula 
Koutinas, Michalis 
Major Field of Science: Natural Sciences
Field Category: Chemical Sciences
Keywords: Ecotoxicological assessment;Enantiomeric excess;Enantiomers;Gene expression;Lupanine;Pseudomonas putida LPK411;Quantitative real-time PCR
Issue Date: 14-Mar-2020
Volume: 19
Issue: 1
Journal: Microbial cell factories 
Abstract: 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: 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: 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.
Description: The article was funded by the “CUT Open Access Author Fund”
ISSN: 1475-2859
DOI: 10.1186/s12934-020-01324-1
Rights: © The Author(s) 2020. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made.
Attribution-NonCommercial-NoDerivatives 4.0 International
Type: Article
Affiliation : Cyprus University of Technology 
University of Cyprus 
Universidade de Lisboa 
Appears in Collections:Άρθρα/Articles

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