A One-Pot Biocatalytic and Organocatalytic Cascade Delivers High Titers of 2-Ethyl-2-Hexenal from n-Butanol

2021 ◽  
Author(s):  
Kelsey Stewart ◽  
Dylan Wythe Domaille
Keyword(s):  
Alcohol Oxidase ◽  
Chemical Transformations ◽  
Chemical Production ◽  
One Pot ◽  
Whole Cell ◽  
Whole Cells ◽  
Whole Cell Biocatalyst ◽  
Selective Chemical ◽  
Initial Results

Biocatalysis provides facile access to selective chemical transformations and helps satisfy sustainable chemical production criteria. However, the reaction scope of biocatalysts is significantly narrower compared to synthetic chemical transformations. Hybrid biocatalytic-chemocatalytic cascades expand the scope of products while maintaining many of the benefits associated with biocatalysis. Here, we report that single-pot systems with whole cell K. pastoris (ATCC® 28485™) or isolated enzyme alcohol oxidase (E 1.1.3.13) as oxidative biocatalysts with a lysine organocatalyst yields the commercial target, 2-ethyl-2-hexenal (2-EH) from n-butanol in a two-step hybrid cascade. Peak yields for both biocatalysts were achieved with 100 mM n-butanol at pH 8 and 30°C. The isolated enzyme slightly outperformed whole cell K. pastoris, reaching 73% conversion (4.7 g/L titers) compared to 61% (3.9 g/L titers) in whole cells systems. Titers could be improved for both biocatalysts (5.7 – 6.7 g/L) at increased butanol loading; however, this came at the expense of decreased yields. Compared to our initial results with a Gluconobactor oxidans whole cell biocatalyst, the reported system improves upon 2-EH titers by 2.8-3.3-fold at maximal yields.

Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids

2018 ◽  
Vol 24 (2) ◽  
pp. 103-107 ◽  
Author(s):  
Anusaya S. Chavan ◽  
Arun S. Kharat ◽  
Manisha R. Bhosle ◽  
Ramrao A. Mane
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Maleic Anhydride ◽  
Baker’S Yeast ◽  
Baker's Yeast ◽  
One Pot ◽  
Whole Cell ◽  
One Pot Synthesis ◽  
Whole Cell Biocatalyst ◽  
Derivatives Of ◽  
Acetic Acids

Abstract An efficient and simple one-pot protocol has been developed for synthesis of substituted derivatives of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a–j and 6a–g by cyclocondensation of aryl/pyrazolyl aldehyde, thiosemicarbazide and maleic anhydride in acetonitrile in the presence of readily available whole cell biocatalyst, baker’s yeast (Saccharomyces cerevisiae). The reaction is enhanced by ultrasonication.

scholarly journals Industrial kinetic resolution of d,l-pantolactone by an immobilized whole-cell biocatalyst

RSC Advances ◽  
2021 ◽  
Vol 11 (48) ◽  
pp. 30373-30376
Author(s):  
Qiu-Hua Zhang ◽  
Liu Yang ◽  
Yi-Bin Tang ◽  
Liu-Nv Huang ◽  
Wen-Fang Luo
Keyword(s):  
Pichia Pastoris ◽  
Calcium Alginate ◽  
Kinetic Resolution ◽  
Whole Cell ◽  
Whole Cells ◽  
Whole Cell Biocatalyst ◽  
Alginate Gels ◽  
Calcium Alginate Gels ◽  
Immobilized Whole Cells

Immobilized whole-cells of Pichia pastoris harboring recombinant d-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution of d,l-pantolactone.

One-pot bio-synthesis of propyl gallate by a novel whole-cell biocatalyst

2014 ◽  
Vol 49 (2) ◽  
pp. 277-282 ◽  
Author(s):  
Guangjun Nie ◽  
Zhiming Zheng ◽  
Wenjin Yue ◽  
Yan Liu ◽  
Hui Liu ◽  
...  
Keyword(s):  
Propyl Gallate ◽  
One Pot ◽  
Whole Cell ◽  
Whole Cell Biocatalyst ◽  
Bio Synthesis

scholarly journals Development of Clostridium saccharoperbutylacetonicum as a Whole Cell Biocatalyst for Production of Chirally Pure (R)-1,3-Butanediol

2021 ◽  
Vol 9 ◽  
Author(s):  
Alexander Grosse-Honebrink ◽  
Gareth T. Little ◽  
Zak Bean ◽  
Dana Heldt ◽  
Ruth H. M. Cornock ◽  
...  
Keyword(s):  
Enzyme Level ◽  
Enantiomeric Excess ◽  
Point Mutations ◽  
Transcriptional Level ◽  
Chemical Production ◽  
Biotechnological Production ◽  
Whole Cell ◽  
Starting Position ◽  
Production Route ◽  
Whole Cell Biocatalyst

Chirally pure (R)-1,3-butanediol ((R)-1,3-BDO) is a valuable intermediate for the production of fragrances, pheromones, insecticides and antibiotics. Biotechnological production results in superior enantiomeric excess over chemical production and is therefore the preferred production route. In this study (R)-1,3-BDO was produced in the industrially important whole cell biocatalyst Clostridium saccharoperbutylacetonicum through expression of the enantio-specific phaB gene from Cupriavidus necator. The heterologous pathway was optimised in three ways: at the transcriptional level choosing strongly expressed promoters and comparing plasmid borne with chromosomal gene expression, at the translational level by optimising the codon usage of the gene to fit the inherent codon adaptation index of C. saccharoperbutylacetonicum, and at the enzyme level by introducing point mutations which led to increased enzymatic activity. The resulting whole cell catalyst produced up to 20 mM (1.8 g/l) (R)-1,3-BDO in non-optimised batch fermentation which is a promising starting position for economical production of this chiral chemical.

scholarly journals Tuning a bi-enzymatic cascade reaction in Escherichia coli to facilitate NADPH regeneration for ε-caprolactone production

2021 ◽  
Vol 8 (1) ◽  
Author(s):  
Jinghui Xiong ◽  
Hefeng Chen ◽  
Ran Liu ◽  
Hao Yu ◽  
Min Zhuo ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Binding Sites ◽  
Regeneration System ◽  
Nadph Regeneration ◽  
Whole Cell ◽  
Cyclohexanone Monooxygenase ◽  
Ribosome Binding ◽  
Ribosome Binding Sites ◽  
Whole Cell Biocatalyst ◽  
Substrate Tolerance

Abstractε-Caprolactone is a monomer of poly(ε-caprolactone) which has been widely used in tissue engineering due to its biodegradability and biocompatibility. To meet the massive demand for this monomer, an efficient whole-cell biocatalytic approach was constructed to boost the ε-caprolactone production using cyclohexanol as substrate. Combining an alcohol dehydrogenase (ADH) with a cyclohexanone monooxygenase (CHMO) in Escherichia coli, a self-sufficient NADPH-cofactor regeneration system was obtained. Furthermore, some improved variants with the better substrate tolerance and higher catalytic ability to ε-caprolactone production were designed by regulating the ribosome binding sites. The best mutant strain exhibited an ε-caprolactone yield of 0.80 mol/mol using 60 mM cyclohexanol as substrate, while the starting strain only got a conversion of 0.38 mol/mol when 20 mM cyclohexanol was supplemented. The engineered whole-cell biocatalyst was used in four sequential batches to achieve a production of 126 mM ε-caprolactone with a high molar yield of 0.78 mol/mol.

Antityrosinase Mechanism and Antimelanogenic Effect of Arbutin Esters Synthesis Catalyzed by Whole-Cell Biocatalyst

2021 ◽  
Vol 69 (14) ◽  
pp. 4243-4252
Author(s):  
Haixia Xu ◽  
Xiaofeng Li ◽  
Xuan Xin ◽  
Lan Mo ◽  
Yucong Zou ◽  
...  
Keyword(s):  
Whole Cell ◽  
Whole Cell Biocatalyst

Enantiocomplementary decarboxylative hydroxylation combining photocatalysis and whole-cell biocatalysis in a one-pot cascade process

2019 ◽  
Vol 21 (8) ◽  
pp. 1907-1911 ◽  
Author(s):  
Jian Xu ◽  
Mamatjan Arkin ◽  
Yongzhen Peng ◽  
Weihua Xu ◽  
Huilei Yu ◽  
...  
Keyword(s):  
Cascade Process ◽  
One Pot ◽  
Whole Cell ◽  
Whole Cell Biocatalysis

The first demonstration of photochemo-enzymatic whole-cell one-pot enantiocomplementary decarboxylative hydroxylation.

scholarly journals Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates

2019 ◽  
Vol 377 (6) ◽  
Author(s):  
Samson Afewerki ◽  
Armando Córdova
Keyword(s):  
Transition Metal ◽  
Metal Complex ◽  
Carbonyl Compounds ◽  
Transition Metal Catalysis ◽  
Chemical Transformations ◽  
Considerable Effort ◽  
Metal Catalysis ◽  
First Report ◽  
Wide Range ◽  
Selective Chemical

AbstractThe concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations not accessible without this combination. The amine catalyst activates the carbonyl compounds through the formation of a reactive nucleophilic enamine intermediate and, in parallel, the transition metal activates a wide range of functionalities such as allylic substrates through the formation of reactive electrophilic π-allyl-metal complex. Since the first report of this strategy in 2006, considerable effort has been devoted to the successful advancement of this technology. In this chapter, these findings are highlighted and discussed.

Engineered whole-cell biocatalyst-based detoxification and detection of neurotoxic organophosphate compounds

2014 ◽  
Vol 32 (3) ◽  
pp. 652-662 ◽  
Author(s):  
Chang Sup Kim ◽  
Jeong Hyun Seo ◽  
Dong Gyun Kang ◽  
Hyung Joon Cha
Keyword(s):  
Whole Cell ◽  
Organophosphate Compounds ◽  
Whole Cell Biocatalyst
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