Carboligation of 5-(hydroxymethyl)furfural via whole-cell catalysis to form C12 furan derivatives and their use for hydrazone formation
Glaser, Sara Jonsdottir LU ; Pyo, Sang-Hyun LU ; Rehnberg, Nicola LU
; Rother, Dörte
and Hatti-Kaul, Rajni
LU
(2023)
In Microbial Cell Factories
22.
- Abstract
BACKGROUND: Biobased 5-(hydroxymethyl)furfural (5-HMF) is an important platform that offers numerous possibilities for upgrading to a range of chemical, material and fuel products. One reaction of special interest is the carboligation of 5-HMF into C 12 compounds, including 5,5'-bis(hydroxymethyl)furoin (DHMF) and its subsequent oxidation to 5,5'-bis(hydroxymethyl)furil (BHMF), due to their potential applications as building blocks for polymers and hydrocarbon fuels.
OBJECTIVES: This study was aimed at evaluating the use of whole cells of Escherichia coli carrying recombinant Pseudomonas fluorescens benzaldehyde lyase as biocatalysts for 5-HMF carboligation, recovery of the C 12 derivatives DHMF and BHMF, and testing the... (More)
BACKGROUND: Biobased 5-(hydroxymethyl)furfural (5-HMF) is an important platform that offers numerous possibilities for upgrading to a range of chemical, material and fuel products. One reaction of special interest is the carboligation of 5-HMF into C 12 compounds, including 5,5'-bis(hydroxymethyl)furoin (DHMF) and its subsequent oxidation to 5,5'-bis(hydroxymethyl)furil (BHMF), due to their potential applications as building blocks for polymers and hydrocarbon fuels.
OBJECTIVES: This study was aimed at evaluating the use of whole cells of Escherichia coli carrying recombinant Pseudomonas fluorescens benzaldehyde lyase as biocatalysts for 5-HMF carboligation, recovery of the C 12 derivatives DHMF and BHMF, and testing the reactivity of the carbonyl groups for hydrazone formation for potential use as cross-linking agents in surface coatings. The effects of different parameters on the reaction were investigated to find the conditions for achieving high product yield and productivity.
RESULTS: The reaction with 5 g/L 5-HMF using 2 g CDW/L recombinant cells in 10% dimethyl carbonate, pH 8.0 at 30 °C resulted in DHMF yield of 81.7% (0.41 mol/mol) at 1 h, and BHMF yield of 96.7% (0.49 mol/mol) at 72 h reaction time. Fed-batch biotransformation generated a maximum DHMF concentration of 53.0 g/L (or 26.5 g DHMF/g cell catalyst) with productivity of 10.6 g/L .h, after five feeds of 20 g/L 5-HMF. Both DHMF and BHMF reacted with adipic acid dihydrazide to form hydrazone that was confirmed by Fourier-transform infrared spectroscopy and 1H NMR.
CONCLUSION: The study demonstrates the potential application of recombinant E. coli cells for cost-effective production of commercially relevant products.
(Less)
- author
- Glaser, Sara Jonsdottir
LU
; Pyo, Sang-Hyun
LU
; Rehnberg, Nicola
LU
; Rother, Dörte
and Hatti-Kaul, Rajni
LU
- organization
- publishing date
- 2023-06-29
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Escherichia coli/genetics, Furans, Catalysis, Hydrazones
- in
- Microbial Cell Factories
- volume
- 22
- article number
- 120
- pages
- 13 pages
- publisher
- BioMed Central (BMC)
- external identifiers
-
- scopus:85163782598
- pmid:37386409
- ISSN
- 1475-2859
- DOI
- 10.1186/s12934-023-02130-1
- language
- English
- LU publication?
- yes
- additional info
- © 2023. The Author(s).
- id
- f2acbdf7-7ad3-4b6a-8e6c-c506ca380aae
- date added to LUP
- 2023-07-08 13:35:41
- date last changed
- 2024-04-20 00:18:34
@article{f2acbdf7-7ad3-4b6a-8e6c-c506ca380aae,
abstract = {{<p>BACKGROUND: Biobased 5-(hydroxymethyl)furfural (5-HMF) is an important platform that offers numerous possibilities for upgrading to a range of chemical, material and fuel products. One reaction of special interest is the carboligation of 5-HMF into C 12 compounds, including 5,5'-bis(hydroxymethyl)furoin (DHMF) and its subsequent oxidation to 5,5'-bis(hydroxymethyl)furil (BHMF), due to their potential applications as building blocks for polymers and hydrocarbon fuels. </p><p>OBJECTIVES: This study was aimed at evaluating the use of whole cells of Escherichia coli carrying recombinant Pseudomonas fluorescens benzaldehyde lyase as biocatalysts for 5-HMF carboligation, recovery of the C 12 derivatives DHMF and BHMF, and testing the reactivity of the carbonyl groups for hydrazone formation for potential use as cross-linking agents in surface coatings. The effects of different parameters on the reaction were investigated to find the conditions for achieving high product yield and productivity. </p><p>RESULTS: The reaction with 5 g/L 5-HMF using 2 g CDW/L recombinant cells in 10% dimethyl carbonate, pH 8.0 at 30 °C resulted in DHMF yield of 81.7% (0.41 mol/mol) at 1 h, and BHMF yield of 96.7% (0.49 mol/mol) at 72 h reaction time. Fed-batch biotransformation generated a maximum DHMF concentration of 53.0 g/L (or 26.5 g DHMF/g cell catalyst) with productivity of 10.6 g/L .h, after five feeds of 20 g/L 5-HMF. Both DHMF and BHMF reacted with adipic acid dihydrazide to form hydrazone that was confirmed by Fourier-transform infrared spectroscopy and 1H NMR. </p><p>CONCLUSION: The study demonstrates the potential application of recombinant E. coli cells for cost-effective production of commercially relevant products.</p>}},
author = {{Glaser, Sara Jonsdottir and Pyo, Sang-Hyun and Rehnberg, Nicola and Rother, Dörte and Hatti-Kaul, Rajni}},
issn = {{1475-2859}},
keywords = {{Escherichia coli/genetics; Furans; Catalysis; Hydrazones}},
language = {{eng}},
month = {{06}},
publisher = {{BioMed Central (BMC)}},
series = {{Microbial Cell Factories}},
title = {{Carboligation of 5-(hydroxymethyl)furfural via whole-cell catalysis to form C12 furan derivatives and their use for hydrazone formation}},
url = {{http://dx.doi.org/10.1186/s12934-023-02130-1}},
doi = {{10.1186/s12934-023-02130-1}},
volume = {{22}},
year = {{2023}},
}