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Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate

A whole-cell based method was developed for the regioselective synthesis of arabinocytosine laurate. Among the seven kinds of bacteria strains tested in the acylation reaction, Pseudomonas fluorescens gave the highest productivity and a higher 5′-regioselectivity than 99%. Compared with pure organic...

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Autores principales: Yang, Meiyan, Wu, Hui, Lian, Yan, Li, Xiaofeng, Lai, Furao, Zhao, Guanglei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4138074/
https://www.ncbi.nlm.nih.gov/pubmed/25136983
http://dx.doi.org/10.1371/journal.pone.0104847
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author Yang, Meiyan
Wu, Hui
Lian, Yan
Li, Xiaofeng
Lai, Furao
Zhao, Guanglei
author_facet Yang, Meiyan
Wu, Hui
Lian, Yan
Li, Xiaofeng
Lai, Furao
Zhao, Guanglei
author_sort Yang, Meiyan
collection PubMed
description A whole-cell based method was developed for the regioselective synthesis of arabinocytosine laurate. Among the seven kinds of bacteria strains tested in the acylation reaction, Pseudomonas fluorescens gave the highest productivity and a higher 5′-regioselectivity than 99%. Compared with pure organic solvents, the use of organic solvent mixtures greatly promoted the yield of the whole-cell catalyzed reaction, but showed little influence on the 5′-regioselectivity. Of all the tested solvent mixtures, the best reaction result was found in isopropyl ether/pyridine followed by isopentanol/pyridine. However, the whole-cells showed much lower thermostability in isopropyl ether/pyridine than in THF-pyridine. To better understand the toxic effects of the organic solvents on P. fluorescens whole-cells and growing cells were further examined. Significant influences of organic solvents on the biomass of the cells were found, which differed depending on the type of solvents used. SEM analysis visually revealed the changes in the surface morphology of whole-cells and growing cells cultured in media containing various organic solvents, in terms of surface smoothness, bulges and changed cell sizes. Results demonstrated that organic toxicity to cell structure played an important role in whole-cell mediated catalysis.
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spelling pubmed-41380742014-08-20 Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate Yang, Meiyan Wu, Hui Lian, Yan Li, Xiaofeng Lai, Furao Zhao, Guanglei PLoS One Research Article A whole-cell based method was developed for the regioselective synthesis of arabinocytosine laurate. Among the seven kinds of bacteria strains tested in the acylation reaction, Pseudomonas fluorescens gave the highest productivity and a higher 5′-regioselectivity than 99%. Compared with pure organic solvents, the use of organic solvent mixtures greatly promoted the yield of the whole-cell catalyzed reaction, but showed little influence on the 5′-regioselectivity. Of all the tested solvent mixtures, the best reaction result was found in isopropyl ether/pyridine followed by isopentanol/pyridine. However, the whole-cells showed much lower thermostability in isopropyl ether/pyridine than in THF-pyridine. To better understand the toxic effects of the organic solvents on P. fluorescens whole-cells and growing cells were further examined. Significant influences of organic solvents on the biomass of the cells were found, which differed depending on the type of solvents used. SEM analysis visually revealed the changes in the surface morphology of whole-cells and growing cells cultured in media containing various organic solvents, in terms of surface smoothness, bulges and changed cell sizes. Results demonstrated that organic toxicity to cell structure played an important role in whole-cell mediated catalysis. Public Library of Science 2014-08-19 /pmc/articles/PMC4138074/ /pubmed/25136983 http://dx.doi.org/10.1371/journal.pone.0104847 Text en © 2014 Yang et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Yang, Meiyan
Wu, Hui
Lian, Yan
Li, Xiaofeng
Lai, Furao
Zhao, Guanglei
Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate
title Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate
title_full Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate
title_fullStr Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate
title_full_unstemmed Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate
title_short Influence of Organic Solvents on Catalytic Behaviors and Cell Morphology of Whole-Cell Biocatalysts for Synthesis of 5′-Arabinocytosine Laurate
title_sort influence of organic solvents on catalytic behaviors and cell morphology of whole-cell biocatalysts for synthesis of 5′-arabinocytosine laurate
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4138074/
https://www.ncbi.nlm.nih.gov/pubmed/25136983
http://dx.doi.org/10.1371/journal.pone.0104847
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