Bio-based production of crotonic acid by pyrolysis of poly(3-hydroxybutyrate) inclusions

Mamat, Mohd Rahimi Zakaria; Ariffin, Hidayah; Hassan, Mohd Ali; Zahari, Mior Ahmad Khushairi Mohd

doi:10.1016/j.jclepro.2014.07.064

Cited by 54 publications

(68 citation statements)

References 26 publications

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“…Efforts have been made to transform fossil-based production of ,-UCAs into more sustainable platforms. For example, a thermochemical method involving isothermal degradation of biologically-generated poly (3-hydroxybutyrate) (PHB) by a Cupriavidus necator strain to produce crotonic acid at a 60% conversion yield has been recently reported (Mamat et al, 2014). As an alternative, purely biological routes can be developed by using microorganisms such as Escherichia coli.…”

Section: Introductionmentioning

confidence: 99%

Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids

Kim

Cheong

González

2016

Metabolic Engineering

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Concerns over sustained availability of fossil resources along with environmental impact of their use have stimulated the development of alternative methods for fuel and chemical production from renewable resources. In this work, we present a new approach to produce α,β-unsaturated carboxylic acids (α,β-UCAs) using an engineered reversal of the β-oxidation (r-BOX) cycle. To increase the availability of both acyl-CoAs and enoyl-CoAs for α,β-UCA production, we use an engineered Escherichia coli strain devoid of mixed-acid fermentation pathways and known thioesterases. Core genes for r-BOX such as thiolase, hydroxyacyl-CoA dehydrogenase, enoyl-CoA hydratase, and enoyl-CoA reductase were chromosomally overexpressed under the control of a cumate inducible phage promoter. Native E. coli thioesterase YdiI was used as the cycle-terminating enzyme, as it was found to have not only the ability to convert trans-enoyl-CoAs to the corresponding α,β-UCAs, but also a very low catalytic efficiency on acetyl-CoA, the primer and extender unit for the r-BOX pathway. Coupling of r-BOX with YdiI led to crotonic acid production at titers reaching 1.5g/L in flask cultures and 3.2g/L in a controlled bioreactor. The engineered r-BOX pathway was also used to achieve for the first time the production of 2-hexenoic acid, 2-octenoic acid, and 2-decenoic acid at a final titer of 0.2g/L. The superior nature of the engineered pathway was further validated through the use of in silico metabolic flux analysis, which showed the ability of r-BOX to support growth-coupled production of α,β-UCAs with a higher ATP efficiency than the widely used fatty acid biosynthesis pathway. Taken together, our findings suggest that r-BOX could be an ideal platform to implement the biological production of α,β-UCAs.

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Section: Introductionmentioning

confidence: 99%

Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids

Kim

Cheong

González

2016

Metabolic Engineering

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“…It remains, however, an open question whether megatons industrial scale production of PHA is economically and environmentally competitive with, e.g., chemical recycling of “oil plastics” produced from biological source material. Even if not, production of PHA monomers for use as green platform chemicals convertible into, e.g., crotonic acid [ 116 ] might prove just as important in a future green biorefinery that utilizes a spectrum of biological processes for substitution of fossil petroleum.…”

Section: Discussionmentioning

confidence: 99%

High natural PHA production from acetate in Cobetia sp. MC34 and Cobetia marina DSM 4741T and in silico analyses of the genus specific PhaC2 polymerase variant

et al. 2021

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Background Several members of the bacterial Halomonadacea family are natural producers of polyhydroxyalkanoates (PHA), which are promising materials for use as biodegradable bioplastics. Type-strain species of Cobetia are designated PHA positive, and recent studies have demonstrated relatively high PHA production for a few strains within this genus. Industrially relevant PHA producers may therefore be present among uncharacterized or less explored members. In this study, we characterized PHA production in two marine Cobetia strains. We further analyzed their genomes to elucidate pha genes and metabolic pathways which may facilitate future optimization of PHA production in these strains. Results Cobetia sp. MC34 and Cobetia marina DSM 4741T were mesophilic, halotolerant, and produced PHA from four pure substrates. Sodium acetate with- and without co-supplementation of sodium valerate resulted in high PHA production titers, with production of up to 2.5 g poly(3-hydroxybutyrate) (PHB)/L and 2.1 g poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV)/L in Cobetia sp. MC34, while C. marina DSM 4741T produced 2.4 g PHB/L and 3.7 g PHBV/L. Cobetia marina DSM 4741T also showed production of 2.5 g PHB/L from glycerol. The genome of Cobetia sp. MC34 was sequenced and phylogenetic analyses revealed closest relationship to Cobetia amphilecti. PHA biosynthesis genes were located at separate loci similar to the arrangement in other Halomonadacea. Further genome analyses revealed some differences in acetate- and propanoate metabolism genes between the two strains. Interestingly, only a single PHA polymerase gene (phaC2) was found in Cobetia sp. MC34, in contrast to two copies (phaC1 and phaC2) in C. marina DSM 4741T. In silico analyses based on phaC genes show that the PhaC2 variant is conserved in Cobetia and contains an extended C-terminus with a high isoelectric point and putative DNA-binding domains. Conclusions Cobetia sp. MC34 and C. marina DSM 4741T are natural producers of PHB and PHBV from industrially relevant pure substrates including acetate. However, further scale up, optimization of growth conditions, or use of metabolic engineering is required to obtain industrially relevant PHA production titers. The putative role of the Cobetia PhaC2 variant in DNA-binding and the potential implications remains to be addressed by in vitro- or in vivo methods.

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“…[ 243 ] Starting from naphta, the overall yield of the process is about 30%. [ 244 ] The cis isomer of CrA, also called isocrotonic acid, is less stable and is not commercially available. Obtaining CrA from bioresources has mainly been studied via three different routes: acetaldehyde production from ethanol, direct fermentation of CrA, and pyrolysis of PHB.…”

Section: Production Of Biobased Acrylates and Analogsmentioning

confidence: 99%

“…[ 46 ] Unpurified PHB from the fermentation broth was suggested as a potential raw material for CrA production. [ 244,265 ] A mild pretreatment of PHB using a diluted NaOH solution improved the yield and purity of crotonic acid, as it presumably provides a catalyst for the reaction. [ 266 ] Scott and co‐workers suggested a thermal treatment of the unpurified PHB with methanol at 200 °C, 18 bars, yielding methyl crotonate with 60% selectivity.…”

Section: Production Of Biobased Acrylates and Analogsmentioning

confidence: 99%

Production and Polymerization of Biobased Acrylates and Analogs

Fouilloux

Thomas

2021

Macromol. Rapid Commun.

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To prepare biobased polymers, particular attention must be paid to the obtention of the monomers from which they are derived. (Meth)acrylates and their analogs constitute such a class of monomers that have been extensively studied due to the wide range of polymers accessible from them. This review therefore aims to highlight the progresses made in the production and polymerization of (meth)acrylates and their analogs. Acrylic acid production from biomass is close to commercialization, as three different high‐potential intermediates are identified: glycerol, lactic acid, and 3‐hydroxypropionic acid. Biobased methacrylic acid is less common, but several promising options are available, such as the decarboxylation of itaconic acid or the dehydration of 2‐hydroxyisobutyric acid. Itaconic acid is also a vinylic monomer of great interest, and polymers derived from it have already found commercial applications. Methylene butyrolactones are promising monomers, obtained from bioresources via three different intermediates: levulinic, succinic, or itaconic acid. Although expensive, methylene butyrolactones have a strong potential for the production of high‐performance polymers. Finally, β‐substituted acrylic monomers, such as cinnamic, fumaric, muconic, or crotonic acid, are also examined, as they provide an original access to biobased materials from various renewable raw materials, such as protein waste, lignin, or wastewater.

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Bio-based production of crotonic acid by pyrolysis of poly(3-hydroxybutyrate) inclusions

Cited by 54 publications

References 26 publications

Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids

Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids

High natural PHA production from acetate in Cobetia sp. MC34 and Cobetia marina DSM 4741T and in silico analyses of the genus specific PhaC2 polymerase variant

Production and Polymerization of Biobased Acrylates and Analogs

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