One-pot biosynthesis of 1,6-hexanediol from cyclohexane by<i>de novo</i>designed cascade biocatalysis

Zhang, Zhongwei; Li, Qian; Wang, Fei; Li, Renjie; Yu, Xiaojuan; Kang, Lixin; Zhao, Jing; Li, Aitao

doi:10.1039/d0gc02600j

Cited by 33 publications

(36 citation statements)

References 36 publications

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“…This approach was selected for two main reasons: the production of the bio-based 1,6-hexanediol (HDO) has been found to reduce greenhouse gas emissions and environmental impacts considerably; and since it can be derived from polysaccharides, the insertion of this diol could promote the biodegradability of copolyesters under the action of specific enzymes, such as Pseudomonas fluorescens. 1,6-Hexanediol (HDO) can be synthesized via hydrogenolytic ring opening of 5-hydroxymethylfurfural (HMF), a dehydration product of hexoses or reducing-end units of polysaccharides [ 48 , 49 ]. 5-Hydroxymethylfurfural (HMF) formation from carbohydrates has been the topic of several studies [ 50 , 51 , 52 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

et al. 2022

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In this work, the feasibility of replacing petroleum-based poly(ethylene terephthalate) (PET) with fully bio-based copolyesters derived from dimethyl 2,5-thiophenedicarboxylate (DMTD), dimethyl 2,5-dimethoxyterephthalate (DMDMT), and polysaccharide-derived 1,6-hexanediol (HDO) was investigated. A systematic study of structure-property relationship revealed that the properties of these poly(thiophene–aromatic) copolyesters (PHS(20–90)) can be tailored by varying the ratio of diester monomers in the reaction, whereby an increase in DMTD content noticeably shortened the reaction time in the transesterification step due to its higher reactivity as compared with DMDMT. The copolyesters had weight-average molar masses (Mw) between 27,500 and 38,800 g/mol, and dispersity Đ of 2.0–2.5. The different polarity and stability of heterocyclic DMTD provided an efficient mean to tailor the crystallization ability of the copolyesters, which in turn affected the thermal and mechanical performance. The glass transition temperature (Tg) could be tuned from 70–100 °C, while the tensile strength was in a range of 23–80 MPa. The obtained results confirmed that the co-monomers were successfully inserted into the copolyester chains. As compared with commercial poly(ethylene terephthalate), the copolyesters displayed not only enhanced susceptibility to hydrolysis, but also appreciable biodegradability by lipases, with weight losses of up to 16% by weight after 28 weeks of incubation.

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Section: Introductionmentioning

confidence: 99%

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

et al. 2022

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“…Thus, cyclohexane supply in a stirred-tank bioreactor is the most critical step to produce monomers. Previous studies either performed shake-flask experiments (Wang et al, 2020;Zhang et al, 2020) or started from the less toxic and less volatile substrate cyclohexanol to produce monomers via cascade reactions (Srinivasamurthy et al, 2019). To exploit the catalytic performance of P. taiwanensis_6HA in a controlled environment enabling high O 2 transfer, a continuous aeration-mediated gaseous cyclohexane feed was established for bioreactor-based biotransformations (Supplementary Figure S3).…”

Section: Substrate Supply and Product Removal As Critical Aspects In Reaction Engineeringmentioning

confidence: 99%

“…Depending on the reaction(s) to be catalyzed, resting cells can be easier to handle and reusable but often suffer from poor stability (Julsing et al, 2012;Zhang et al, 2012). Recently, mixed-species concepts have been used to produce the monomer adipic acid, 6-aminohexanoic acid, or 1,6-hexanediol from cyclohexane (Wang et al, 2020;Zhang et al, 2020;Bretschneider et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

Conversion of Cyclohexane to 6-Hydroxyhexanoic Acid Using Recombinant Pseudomonas taiwanensis in a Stirred-Tank Bioreactor

et al. 2021

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6-hydroxyhexanoic acid (6HA) represents a polymer building block for the biodegradable polymer polycaprolactone. Alternatively to energy- and emission-intensive multistep chemical synthesis, it can be synthesized directly from cyclohexane in one step by recombinant Pseudomonas taiwanensis harboring a 4-step enzymatic cascade without the accumulation of any intermediate. In the present work, we performed a physiological characterization of this strain in different growth media and evaluated the resulting whole-cell activities. RB and M9* media led to reduced gluconate accumulation from glucose compared to M9 medium and allowed specific activities up to 37.5 ± 0.4 U gCDW−1 for 6HA synthesis. However, 50% of the specific activity was lost within 1 h in metabolically active resting cells, specifying growing cells, or induced resting cells as favored options for long-term biotransformation. Furthermore, the whole-cell biocatalyst was evaluated in a stirred-tank bioreactor setup with a continuous cyclohexane supply via the gas phase. At cyclohexane feed rates of 0.276 and 1.626 mmol min−1 L−1, whole-cell biotransformation occurred at first-order and zero-order rates, respectively. A final 6HA concentration of 25 mM (3.3 g L−1) and a specific product yield of 0.4 g gCDW−1 were achieved with the higher feed rate. Product inhibition and substrate toxification were identified as critical factors limiting biocatalytic performance. Future research efforts on these factors and the precise adjustment of the cyclohexane feed combined with an in situ product removal strategy are discussed as promising strategies to enhance biocatalyst durability and product titer and thus to enable the development of a sustainable multistep whole-cell process.

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“…The cognate consortium strategy used in this study corroborates very recent studies that demonstrated the ability of microbial consortia to relieve the metabolic burden of complex pathways when a single strain is used in biotransformations. By segregating biocatalytic pathway into three basic E. coli strains, hence constructing a cognate consortium, aliphatic α,ω-dicarboxylic acids (DCAs) (Wang et al, 2020) and 1,6-hexanediol (HDO) (Zhang et al, 2020) were produced at signi cantly higher rates than using a monoculture system.…”

Section: Optimizing Aeration To Improve Bb Synthesismentioning

confidence: 99%

One-pot production of butyl butyrate from glucose using a cognate “diamond-shaped” E. coli consortium

Sinumvayo

Zhao

Liu

et al. 2021

Preprint

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Esters are widely used in plastics, textile fibers, and general petrochemicals. Usually, esters are produced via chemical synthesis or enzymatic processes from the corresponding alcohols and acids. However, the fermentative production of esters from alcohols and/or acids has recently also become feasible. Here we report a cognate microbial consortium capable of producing butyl butyrate. This microbial consortium consists of two engineered butyrate- and butanol-producing E. coli strains with nearly identical genetic background. The pathways for the synthesis of butyrate and butanol from butyryl-CoA in the respective E. coli strains, together with a lipase-catalyzed esterification reaction, created a “diamond-shaped” consortium. The concentration of butyrate and butanol in the fermentation vessel could be altered by adjusting the inoculation ratios of each E. coli strain in the consortium. After optimization, the consortium produced 7.2 g/L butyl butyrate with a yield of 0.12 g/g glucose without the exogenous addition of butanol or butyrate. To our best knowledge, this is the highest titer and yield of butyl butyrate produced by E. coli reported to date. This study thus provides a new way for the biotechnological production of esters.

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One-pot biosynthesis of 1,6-hexanediol from cyclohexane byde novodesigned cascade biocatalysis

Abstract: 1,6-Hexanediol (HDO) is an important precursor in the polymer industry. The current industrial route to produce HDO involves energy intensive and hazardous multistage (four-pot–four-step) chemical reactions using cyclohexane (CH) as...

Cited by 33 publications

References 36 publications

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

Conversion of Cyclohexane to 6-Hydroxyhexanoic Acid Using Recombinant Pseudomonas taiwanensis in a Stirred-Tank Bioreactor

One-pot production of butyl butyrate from glucose using a cognate “diamond-shaped” E. coli consortium

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