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

2021 ◽  
Vol 8 (1) ◽  
Author(s):  
Jean Paul Sinumvayo ◽  
Chunhua Zhao ◽  
Guoxia Liu ◽  
Yin Li ◽  
Yanping Zhang
Keyword(s):  
Genetic Background ◽  
Microbial Consortium ◽  
Esterification Reaction ◽  
Biotechnological Production ◽  
One Pot ◽  
Butyl Butyrate ◽  
E Coli ◽  
Fermentative Production ◽  
Fermentation Vessel ◽  
Exogenous Addition

AbstractEsters 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.

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

2021 ◽  
Author(s):  
Jean Paul Sinumvayo ◽  
Chunhua Zhao ◽  
Guoxia Liu ◽  
Yin Li ◽  
Yanping Zhang
Keyword(s):  
Microbial Consortium ◽  
Coli Strain ◽  
Esterification Reaction ◽  
Biotechnological Production ◽  
One Pot ◽  
Butyl Butyrate ◽  
E Coli ◽  
Fermentative Production ◽  
Fermentation Vessel ◽  
Exogenous Addition

Abstract 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.

scholarly journals One-pot Production of Butyl Butyrate From Glucose by Constructing a “Diamond-Shaped” E. Coli Consortium

2020 ◽  
Author(s):  
Jean Paul Sinumvayo ◽  
Chunhua Zhao ◽  
Guoxia Liu ◽  
Yanping Zhang ◽  
Yin Li
Keyword(s):  
Chemical Synthesis ◽  
Microbial Consortium ◽  
Esterification Reaction ◽  
Biotechnological Production ◽  
One Pot ◽  
Butyl Butyrate ◽  
E Coli ◽  
Exogenous Addition ◽  
Ester Biosynthesis

Abstract Esters are widely used in plastic, texture, fiber, and petroleum industries. Usually, esters are produced from chemical synthesis or enzymatic processes from the corresponding alcohols and acids. Recently, fermentation production of esters was developed with supplementation of precursors (either alcohol or acid, or both at once). Here using butyl butyrate as an example, we demonstrated that we can use a microbial consortium developed from two engineered butyrate- and butanol-producing E. coli strains for the production of ester, with the assistance of exogenously added lipase. The synthesizing pathways for both precursors and the lipase-based esterification reaction created a “diamond-shaped” consortium. The concentration of the precursors for ester biosynthesis could be altered by adjusting the ratio of the inoculum of each E. coli strain in the consortium. Upon appropriate optimization, the consortium produced 7.2 g/L butyl butyrate without the exogenous addition of butanol or butyrate, which is the highest titer of butyl butyrate produced by E. coli reported to date. This study thus provides a new way for the biotechnological production of esters.

scholarly journals Microbial production of butyl butyrate: from single strain to cognate consortium

2021 ◽  
Vol 8 (1) ◽  
Author(s):  
Jean Paul Sinumvayo ◽  
Yin Li ◽  
Yanping Zhang
Keyword(s):  
Chemical Synthesis ◽  
Microbial Consortium ◽  
Microbial Production ◽  
Single Strain ◽  
Butyl Butyrate ◽  
E Coli ◽  
Adverse Impacts ◽  
Important Chemical ◽  
Alternative Approach

AbstractButyl butyrate (BB) is an important chemical with versatile applications in beverage, food and cosmetics industries. Since chemical synthesis of BB may cause adverse impacts on the environment, biotechnology is an emerging alternative approach for microbial esters biosynthesis. BB can be synthesized by using a single Clostridium strain natively producing butanol or butyrate, with exogenously supplemented butyrate or butanol, in the presence of lipase. Recently, E. coli strains have been engineered to produce BB, but the titer and yield remained very low. This review highlighted a new trend of developing cognate microbial consortium for BB production and associated challenges, and end up with new prospects for further improvement for microbial BB biosynthesis.

scholarly journals A STATISTICAL APPROACH FOR OPTIMIZING THE HIGH YIELD GREEN PRODUCTION OF THE FLAVOR ESTER BUTYL BUTYRATE

2017 ◽  
Vol 79 (7) ◽  
Author(s):  
Ida Nurhazwani Abd Rahman ◽  
Fatin Myra Abd Manan ◽  
Nur Haziqah Che Marzuki ◽  
Naji A. Mahat ◽  
Nursyafreena Attan ◽  
...  
Keyword(s):  
Molar Ratio ◽  
High Yield ◽  
Esterification Reaction ◽  
Reaction Parameters ◽  
Chemical Route ◽  
Butyl Butyrate ◽  
Novozyme 435 ◽  
Yield Production ◽  
Green Production ◽  
Percentage Conversion

Being the prevailing approach for producing esters such as butyl butyrate, the use of chemical route has been linked to numerous disadvantages. Hence, a green alternative method for higher yield production of butyl butyrate by esterification reaction utilizing Novozyme 435 as biocatalysts in a solvent-less system may prove useful. Such approach can be further improved by optimizing the relevant reaction parameters using the Response Surface Methodology by the Box-Benkhen Design attempted in this present study. The reaction parameters evaluated were: substrate molar ratio, time and temperature, and the response of each parameter was measured as percentage conversion yield. Using the Design Expert 7.1.6 optimization functions, the two sets of optimum conditions selected viz. [i] molar ratio butyric acid:butanol 1:3.93, 9.93 h at 56.09°C and [ii] molar ratio butyric acid:butanol 1:3.35, 9.79 h at 53.90°C had afforded the highest yield of butyl butyrate i.e. 99.62% and 99.55%, respectively. The ester product obtained from the reaction were confirmed as butyl butyrate by FTIR and GC. Therefore, the results substantiated the applicability of the RSM prediction technique as well as efficacy of Novozyme 435 as biocatalysts in the high yield solvent-less synthesis of butyl butyrate, adhering to the philosophy of Green Chemistry.

scholarly journals PREPARASI DAN MODIFIKASI KIMIA STRUKTUR KITOOLIGOSAKARIDA-2,5-ANHIDRO-D-MANNOFURANOSA (KOSAMF) DARI KITOSAN SERTA UJI ANTIBAKTERI TERHADAP Staphylococcus aureus DAN Escherichia coli

2016 ◽  
Vol 9 (2) ◽  
pp. 15
Author(s):  
Emil Salim ◽  
Hasnirwan ◽  
Sanusi Ibrahim ◽  
Afrizal
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
One Pot ◽  
E Coli ◽  
Ft Ir

Kitooligosakarida-2,5-anhidro-D-mannofuranosa (KOSamf) dipersiapkan dengan derajat polimerisasi tertentu melalui reaksi nitrous deaminasi dari kitosan parsial N-deasetilasi. KOSamf kemudian diubah menjadi turunan KOSamf dengan mengkopling gugus aldehid yang terdapat pada unit 2,5-anhidro-D-mannofuranosa (amf). KOSamf dengan 3,5-dikloroanilin dan NaBH3CN dalam pelarut buffer ammonium asetat direaksikan melalui metoda one-pot aminasi reduktif untuk menghasilkan turunan KOSamf yang berpotensi sebagai senyawa antibakteri dan antijamur. Struktur kimia dari turunan KOSamf yang telah disintesis dikarakterisasi dengan Spektroskopi FT-IR dan NMR. Senyawa turunan KOSamf memiliki aktivitas sebagai antibakteri terhadap bakteri Staphylococcus aureus dengan zona inhibisi 12,5 mm dan bakteri E. coli dengan zona inhibisi 10,5 mm.

scholarly journals Synthesis, Characterization and in vitro Antimicrobial Screening of Some Novel Series of 2-Azetidinone Derivatives Integrated with Quinoline, Pyrazole and Benzofuran Moieties

2020 ◽  
Vol 32 (4) ◽  
pp. 896-900
Author(s):  
M. Idrees ◽  
Y.G. Bodkhe ◽  
N.J. Siddiqui ◽  
S.S. Kola
Keyword(s):  
Mass Spectra ◽  
Pathogenic Bacteria ◽  
Catalytic Amount ◽  
Spectral Studies ◽  
One Pot ◽  
E Coli ◽  
One Pot Condensation ◽  
Cyclocondensation Reaction ◽  
In Vitro Antibacterial Activity

A series of 5-(benzofuran-2-yl)-N-(3-chloro-4-(2-(p-tolyloxy) substituted quinolin-3-yl)-2-oxoazetidin-1-yl)-1-phenyl-1H-pyrazole-3-carboxamide derivatives (4a-f) were synthesized with excellent yields by cyclocondensation reaction of 5-(benzofuran-2-yl)-N′-(2-(p-tolyloxy) substituted quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbohydrazide (3a-f) with chloroacetyl chloride in presence of triethylamine in DMF. One pot condensation of 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (1) with 2-(p-tolyloxy) substituted quinoline-3-carbaldehyde (2a-f) in ethanol solvent in presence of catalytic amount of acetic acid gave intermediate compounds (3a-f). The structures of newly synthesized compounds have been substantiated through elemental analysis and spectral studies viz. 1H NMR, 13C NMR, IR and mass spectra. All the synthesized compounds were screened for their in vitro antibacterial activity against pathogenic bacteria such as S. aureus and E. coli at different concentrations.

scholarly journals Polyamine-Mediated Resistance of Uropathogenic Escherichia coli to Nitrosative Stress

2006 ◽  
Vol 188 (3) ◽  
pp. 928-933 ◽  
Author(s):  
Jean M. Bower ◽  
Matthew A. Mulvey
Keyword(s):  
Escherichia Coli ◽  
Nitrosative Stress ◽  
Resistance Mutation ◽  
Reactive Nitrogen ◽  
E Coli ◽  
Exogenous Addition ◽  
Reactive Nitrogen Intermediates ◽  
Transposon Mutants ◽  
Increased Sensitivity ◽  
K 12

ABSTRACT During the course of a urinary tract infection, substantial levels of nitric oxide and reactive nitrogen intermediates are generated. We have found that many uropathogenic strains of Escherichia coli display far greater resistance to nitrosative stress than the K-12 reference strain MG1655. By selecting and screening for uropathogenic E. coli transposon mutants that are unable to grow in the presence of acidified nitrite, the cadC gene product was identified as a key facilitator of nitrosative stress resistance. Mutation of cadC, or its transcriptional targets cadA and cadB, results in loss of significant production of the polyamine cadaverine and increased sensitivity to acidified nitrite. Exogenous addition of cadaverine or other polyamines rescues growth of cad mutants under nitrosative stress. In wild-type cells, the concentration of cadaverine produced per cell is substantially increased by exposure to acidified nitrite. The mechanism behind polyamine-mediated rescue from nitrosative stress is unclear, but it is not attributable solely to chemical quenching of reactive nitrogen species or reduction in mutation frequency.

One-Pot Multienzymatic Transformation of NH3, CO2, and Ornithine into the Organic Nitrogen Plant Fertilizer Citrulline Using a Single Recombinant Lysate of E. coli

2019 ◽  
Vol 7 (9) ◽  
pp. 8522-8529 ◽  
Author(s):  
Apostolos Alissandratos ◽  
Carol J. Hartley ◽  
Nigel G. French ◽  
Hye-Kyung Kim ◽  
Susan Allen ◽  
...  
Keyword(s):  
Organic Nitrogen ◽  
One Pot ◽  
E Coli ◽  
Nitrogen Plant

scholarly journals Synthesis and antimicrobial screening of pyrano[3,2-c]chromene derivatives of 1H-pyrazoles

2011 ◽  
Vol 9 (4) ◽  
pp. 635-647 ◽  
Author(s):  
Chetan Sangani ◽  
Divyesh Mungra ◽  
Manish Patel ◽  
Ranjan Patel
Keyword(s):  
Antifungal Activity ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Fungal Pathogens ◽  
Broth Microdilution ◽  
One Pot ◽  
E Coli ◽  
Cyclocondensation Reaction ◽  
Ft Ir ◽  
Derivatives Of

AbstractA new series of twenty four derivatives of pyrano[3,2-c]chromene IVa-x bearing 1H-pyrazole were synthesized by a one pot, base-catalyzed cyclocondensation reaction of 1H-pyrazole-4-carbaldehyde Ia-l, malononitrile II and 4-hydroxycoumarin IIIa-b. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR spectral data. All the synthesized compounds were screened against six bacterial pathogens, namely B. subtilis, C. tetani, S. pneumoniae, S. typhi, V. cholerae, E. coli and for antifungal activity against two fungal pathogens, A. fumigatus and C. albicans using the broth microdilution MIC method. Some of the compounds were found to be equipotent or more potent than commercial drugs against most of employed strains, as evident from the screening data.

scholarly journals The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases

2014 ◽  
Vol 10 ◽  
pp. 1657-1669 ◽  
Author(s):  
Ilja V Fateev ◽  
Konstantin V Antonov ◽  
Irina D Konstantinova ◽  
Tatyana I Muravyova ◽  
Frank Seela ◽  
...  
Keyword(s):  
Electronic Structure ◽  
Chemical Synthesis ◽  
Purine Nucleoside Phosphorylase ◽  
Substrate Recognition ◽  
Chemoenzymatic Synthesis ◽  
Similar Reaction ◽  
One Pot ◽  
E Coli ◽  
Enzymatic Transformation ◽  
Nucleoside Phosphorylases

Two approaches to the synthesis of 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (1, clofarabine) were studied. The first approach consists in the chemical synthesis of 2-deoxy-2-fluoro-α-D-arabinofuranose-1-phosphate (12a, 2FAra-1P) via three step conversion of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (9) into the phosphate 12a without isolation of intermediary products. Condensation of 12a with 2-chloroadenine catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP) resulted in the formation of clofarabine in 67% yield. The reaction was also studied with a number of purine bases (2-aminoadenine and hypoxanthine), their analogues (5-aza-7-deazaguanine and 8-aza-7-deazahypoxanthine) and thymine. The results were compared with those of a similar reaction with α-D-arabinofuranose-1-phosphate (13a, Ara-1P). Differences of the reactivity of various substrates were analyzed by ab initio calculations in terms of the electronic structure (natural purines vs analogues) and stereochemical features (2FAra-1P vs Ara-1P) of the studied compounds to determine the substrate recognition by E. coli nucleoside phosphorylases. The second approach starts with the cascade one-pot enzymatic transformation of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a, followed by its condensation with 2-chloroadenine thereby affording clofarabine in ca. 48% yield in 24 h. The following recombinant E. coli enzymes catalyze the sequential conversion of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a: ribokinase (2-deoxy-2-fluoro-D-arabinofuranose-5-phosphate), phosphopentomutase (PPN; no 1,6-diphosphates of D-hexoses as co-factors required) (12a), and finally PNP. The substrate activities of D-arabinose, D-ribose and D-xylose in the similar cascade syntheses of the relevant 2-chloroadenine nucleosides were studied and compared with the activities of 2-deoxy-2-fluoro-D-arabinose. As expected, D-ribose exhibited the best substrate activity [90% yield of 2-chloroadenosine (8) in 30 min], D-arabinose reached an equilibrium at a concentration of ca. 1:1 of a starting base and the formed 2-chloro-9-(β-D-arabinofuranosyl)adenine (6) in 45 min, the formation of 2-chloro-9-(β-D-xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h.

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