Linked strategy for the production of fuels via formose reaction

Deng, Jin; Pan, Tao; Xu, Qing; Zhang, Ying; Guo, Qi; Fu, Yao

doi:10.1038/srep01244

Cited by 29 publications

(33 citation statements)

References 27 publications

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“…RhaD and FucA from E. coli have been crystallized and showed a strict 3R-stereoselectivity due to mechanistic requirements [ 26 , 27 ]. Therefore, those two enzymes shared identical product termed as dendroketose and can be obtained by self-aldolization of DHA using chemical method [ 19 ]. Enzymes TagA and FruA from E. coli failed to catalyze aldol addition to DHA.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of 2,5-dimethylfuran (DMF) from 5-HMF is a highly attractive route to a renewable fuel [ 18 ]. The feasibility of producing 2,4-dimethylfuran (2,4-DMF) or C 9 –C 15 branched-chain alkanes as liquid transportation fuels from 4-HMF has also been demonstrated [ 19 ]. Therefore, developing methods that can synthesize branched-chain sugar is meaningful.…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of dendroketose from different carbon sources using in vitro and in vivo metabolic engineering strategies

Yang

Zhu

et al. 2018

Biotechnol Biofuels

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BackgroundAsymmetric aldol-type C–C bond formation with ketones used as electrophilic receptor remains a challenging reaction for aldolases as biocatalysts. To date, only one kind of dihydroxyacetone phosphate (DHAP)-dependent aldolases has been discovered and applied to synthesize branched-chain sugars directly using DHAP and dihydroxyacetone (DHA) as substrate. However, the unstable and high-cost properties of DHAP limit large-scale application. Therefore, biosynthesis of branched-chain sugar from low-cost and abundant carbon sources is essential.ResultsThe detailed catalytic property of l-rhamnulose-1-phosphate aldolase (RhaD) and l-fuculose-1-phosphate aldolase (FucA) from Escherichia coli in catalyzing the aldol reactions with DHA as electrophilic receptors was characterized. Furthermore, we calculated the Bürgi–Dunitz trajectory using molecular dynamics simulations, thereby revealing the original sources of the catalytic efficiency of RhaD and FucA. A multi-enzyme reaction system composed of formolase, DHA kinase, RhaD, fructose-1-phosphatase, and polyphosphate kinase was constructed to in vitro produce dendroketose, a branched-chain sugar, from one-carbon formaldehyde. The conversion rate reached 86% through employing a one-pot, two-stage reaction process. Moreover, we constructed two artificial pathways in Corynebacterium glutamicum to obtain this product in vivo starting from glucose or glycerol. Fermentation with glycerol as feedstock produced 6.4 g/L dendroketose with a yield of 0.45 mol/mol glycerol, representing 90% of the maximum theoretical value. Additionally, the dendroketose production reached 36.3 g/L with a yield of 0.46 mol/mol glucose when glucose served as the sole carbon resource.ConclusionsThe detailed enzyme kinetics data of the two DHAP-dependent aldolases with DHA as electrophilic receptors were presented in this study. In addition, insights into this catalytic property were given via in silico simulations. Moreover, the cost-effective synthesis of dendroketose starting from one-, three-, and six-carbon resources was achieved through in vivo and in vitro metabolic engineering strategies. This rare branched-chain ketohexose may serve as precursor to prepare 4-hydroxymethylfurfural and branched-chain alkanes using chemical method.Electronic supplementary materialThe online version of this article (10.1186/s13068-018-1293-7) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biosynthesis of dendroketose from different carbon sources using in vitro and in vivo metabolic engineering strategies

Yang

Zhu

et al. 2018

Biotechnol Biofuels

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“…The phosphorylated form of this triose (DHA-3-phosphate; DHA-P) is an intermediate of glycolysis. DHA can be catalytically produced from formaldehyde by the formose reaction (2)(3)(4) for fermentation by appropriately engineered microbial biocatalysts to any number of chemical and fuel molecules, such as ethanol, butanol, lactate, and succinate, among others. (Fig.…”

mentioning

confidence: 99%

Fermentation of dihydroxyacetone by engineered Escherichia coli and Klebsiella variicola to products

Wang

Chauliac

Rhee

et al. 2018

Proc. Natl. Acad. Sci. U.S.A.

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Methane can be converted to triose dihydroxyacetone (DHA) by chemical processes with formaldehyde as an intermediate. Carbon dioxide, a by-product of various industries including ethanol/butanol biorefineries, can also be converted to formaldehyde and then to DHA. DHA, upon entry into a cell and phosphorylation to DHA-3-phosphate, enters the glycolytic pathway and can be fermented to any one of several products. However, DHA is inhibitory to microbes due to its chemical interaction with cellular components. Fermentation of DHA to d-lactate by strain TG113 was inefficient, and growth was inhibited by 30 g⋅L DHA. An ATP-dependent DHA kinase from (pDC117d) permitted growth of strain TG113 in a medium with 30 g⋅L DHA, and in a fed-batch fermentation the d-lactate titer of TG113(pDC117d) was 580 ± 21 mM at a yield of 0.92 g⋅g DHA fermented. strain LW225, with a higher glucose flux than, produced 811 ± 26 mM d-lactic acid at an average volumetric productivity of 2.0 g⋅L⋅h Fermentation of DHA required a balance between transport of the triose and utilization by the microorganism. Using other engineered strains, we also fermented DHA to succinic acid and ethanol, demonstrating the potential of converting CH and CO to value-added chemicals and fuels by a combination of chemical/biological processes.

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“…The above-mentioned reactions based on an aldol reaction between the biomass-derived oxygenates (e.g., glycolaldehyde (GA)) are comparable to the formose reaction, in which sugars are prepared from formaldehyde and a sequential aldol condensation (Scheme 7) [20,21,22,23,24,25]. Although application of the formose reaction has previously been confined to the selective synthesis of unprotected sugars, an intermolecular coupling reaction between GA (C2) and oxygenates of different carbon numbers will increase the number of potential products.…”

Section: Cascade Synthesis Using Biomass-derived Oxygenates As Carmentioning

confidence: 99%

A Novel Strategy for Biomass Upgrade: Cascade Approach to the Synthesis of Useful Compounds via C-C Bond Formation Using Biomass-Derived Sugars as Carbon Nucleophiles

Yamaguchi

Baba

2016

Molecules

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Due to the depletion of fossil fuels, biomass-derived sugars have attracted increasing attention in recent years as an alternative carbon source. Although significant advances have been reported in the development of catalysts for the conversion of carbohydrates into key chemicals (e.g., degradation approaches based on the dehydration of hydroxyl groups or cleavage of C-C bonds via retro-aldol reactions), only a limited range of products can be obtained through such processes. Thus, the development of a novel and efficient strategy targeted towards the preparation of a range of compounds from biomass-derived sugars is required. We herein describe the highly-selective cascade syntheses of a range of useful compounds using biomass-derived sugars as carbon nucleophiles. We focus on the upgrade of C2 and C3 oxygenates generated from glucose to yield useful compounds via C-C bond formation. The establishment of this novel synthetic methodology to generate valuable chemical products from monosaccharides and their decomposed oxygenated materials renders carbohydrates a potential alternative carbon resource to fossil fuels.

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Linked strategy for the production of fuels via formose reaction

Cited by 29 publications

References 27 publications

Biosynthesis of dendroketose from different carbon sources using in vitro and in vivo metabolic engineering strategies

Biosynthesis of dendroketose from different carbon sources using in vitro and in vivo metabolic engineering strategies

Fermentation of dihydroxyacetone by engineered Escherichia coli and Klebsiella variicola to products

A Novel Strategy for Biomass Upgrade: Cascade Approach to the Synthesis of Useful Compounds via C-C Bond Formation Using Biomass-Derived Sugars as Carbon Nucleophiles

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