Enzymatic synthesis of cephalothin by penicillin G acylase*

Abstract:

:Enzymatic synthesis of cephalothin from 7-aminocephalosporanic acid (7-ACA) and amide derivatives of 2-thienylacetic acid (2-TA) using penicillin G acylase (pen G acylase) was studied. Two amide derivatives of 2-TA namely 2-thienylacetamide (2-TAA) and 2-thienylacetohydroxamic acid (2-TAH) were used in this study. The main reason for choosing amide but not the methyl ester derivative of 2-TA for the enzymatic synthesis was to increase their solubilities in water. The solubility of 2-TA methyl ester (2-TAM), 2-TAA, and 2-TAH in aqueous solution is 8 +/- 0.05 mM, 87 +/- 0.75 mM and 120 +/- 1.65 mM, respectively. Enzymatic conversion of 2-TAH to cephalothin yielded side products but they were not found in the conversion of 2-TAA to cephalothin. The side products were derived from reactions between hydroxyamine and 7-ACA. The effects of pH, temperature, initial substrate concentrations and reaction time on the conversion of 2-TAA and 7-ACA to cephalothin were examined. The optimum reaction condition was determined at pH 6.5 and 10 approximately 15 degrees C. The best conversion yield of 72% was obtained when the initial concentration of 2-TAA and 7-ACA was at 0.4 M and 0.1 M, respectively. Furthermore, a one-step method was developed to purify cephalothin from the enzymatic reaction mixture with the purity of 91% and the recovery yield of 96%.

journal_name

Enzyme Microb Technol

authors

Shaw S,Shyu J,Hsieh Y,Yeh H

doi

10.1016/s0141-0229(99)00153-2

keywords:

subject

Has Abstract

pub_date

2000-02-01 00:00:00

pages

142-151

issue

2-4

eissn

0141-0229

issn

1879-0909

pii

S0141022999001532

journal_volume

26

pub_type

杂志文章
  • Effect of intense pulsed light on the deactivation of lipase: Enzyme-deactivation kinetics and tertiary structural changes by fragmentation.

    abstract::The effect of intense pulsed light (IPL) irradiation on Chromobacterium viscosum lipase was investigated with a primary focus on catalytic activity and molecular structure. During IPL irradiation, lipase activity decreased significantly with increasing pulse fluence (Fp) and exposure time (te). IPL-induced deactivatio...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2019.02.001

    authors: Jeon MS,Park KM,Yu H,Park JY,Chang PS

    更新日期:2019-05-01 00:00:00

  • A new pH indicator dye-based method for rapid and efficient screening of l-asparaginase producing microorganisms.

    abstract::l-asparaginase is a pharmaceutically and industrially important enzyme as it has potential to treat different cancers and inhibit acrylamide formation in fried and baked food products. In the present study, an attempt was made to screen for new and novel l-asparaginase producers using a widely applied phenol red and b...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2017.08.004

    authors: Mihooliya KN,Nandal J,Swami L,Verma H,Chopra L,Sahoo DK

    更新日期:2017-12-01 00:00:00

  • Oxygen derepresses deacetoxycephalosporin C synthase and increases the conversion of penicillin N to cephamycin C in Streptomyces clavuligerus.

    abstract::When dissolved oxygen (DO) was maintained at saturation level during batch fermentations of Streptomyces clavuligerus (NRRL 3585), the accumulation of the intermediate penicillin N was lowered while formation of the end product cephamycin C was increased relative to fermentations without DO control. The specific activ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/0141-0229(90)90178-s

    authors: Rollins MJ,Jensen SE,Wolfe S,Westlake DW

    更新日期:1990-01-01 00:00:00

  • Stability of a recombinant shuttle plasmid in Bacillus subtilis and Escherichia coli.

    abstract::The recombinant shuttle plasmid pCPPS-31, which confers carboxymethylcellulase (CMCase) production and neomycin resistance (Ner), was segregationally but not structurally unstable in both B. subtilis (50-60%) and Escherichia coli (80-90%) when grown in serial batch cultures for 72 h diluting 1:1,000 with fresh medium ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/0141-0229(94)90049-3

    authors: Vyas VV,Gupta S,Sharma P

    更新日期:1994-03-01 00:00:00

  • Construction of glutamate biosensor based on covalent immobilization of glutamate oxidase on polypyrrole nanoparticles/polyaniline modified gold electrode.

    abstract::A method is described for construction of a highly sensitive electrochemical biosensor for detection of glutamate. The biosensor is based on covalent immobilization of glutamate oxidase (GluOx) onto polypyrrole nanoparticles and polyaniline composite film (PPyNPs/PANI) electrodeposited onto Au electrode. The enzyme el...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2014.02.001

    authors: Batra B,Kumari S,Pundir CS

    更新日期:2014-04-10 00:00:00

  • Structural characterization and biological evaluation of Staphylosan (dimannooleate), a new glycolipid surfactant produced by a marine Staphylococcus saprophyticus SBPS-15.

    abstract::Marine microbes have gained significant attention as potential biofactories for broad spectrum bioactive compounds. In the recent years, bioactive biosurfactants have warranted renewed interest from both environmental and clinical sectors as anti-biofilm agents due to their excellent properties of dispersing microbial...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2018.09.008

    authors: Balan SS,Mani P,Kumar CG,Jayalakshmi S

    更新日期:2019-01-01 00:00:00

  • Characterization of specificity of subtilisin Carlsberg towards peptide T by high-performance liquid chromatography and electrospray mass spectrometry.

    abstract::Peptide T has a sequence (Ala-Ser-Thr-Thr-Thr-Asn-Tyr-Thr) belonging to HIV envelope that is involved in the interaction with CD(4) receptor of T lymphocytes. Research of protease activities towards this peptide is very relevant for AIDS therapy. Characterization of specificity of subtilisin Carlsberg towards this ver...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(99)00170-2

    authors: Nedjar-Arroumea N,Paon M,Koralewski F,Friboulet A,Kouach M,Briand G,Leroy Y,Guillochon D

    更新日期:2000-03-01 00:00:00

  • Aspergillus niger I-1472 and Pycnoporus cinnabarinus MUCL39533, selected for the biotransformation of ferulic acid to vanillin, are also able to produce cell wall polysaccharide-degrading enzymes and feruloyl esterases.

    abstract::The filamentous fungal strains Aspergillus niger I-1472 and Pycnoporus cinnabarinus MUCL39533, previously selected for the bioconversion of ferulic acid to vanillic acid and vanillin respectively, were grown on sugar beet pulp. A large spectrum of polysaccharide-degrading enzymes was produced by A. niger and very few ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(00)00277-5

    authors: Bonnina E,Brunel M,Gouy Y,Lesage-Meessen L,Asther M,Thibault J

    更新日期:2001-01-02 00:00:00

  • Covalent immobilization of catalase onto spacer-arm attached modified florisil: characterization and application to batch and plug-flow type reactor systems.

    abstract::Catalase was covalently immobilized onto florisil via glutaraldehyde (GA) and glutaraldehyde+6-amino hexanoic acid (6-AHA) (as a spacer arm). Immobilizations of catalase onto modified supports were optimized to improve the efficiency of the overall immobilization procedures. The V(max) values of catalase immobilized v...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2011.09.002

    authors: Alptekin O,Tükel SS,Yildirim D,Alagöz D

    更新日期:2011-12-10 00:00:00

  • Identification and catalytic properties of new epoxide hydrolases from the genomic data of soil bacteria.

    abstract::Epoxide hydrolases (EHs) catalyse the conversion of epoxides into vicinal diols. These enzymes have extensive value in biocatalysis as they can generate enantiopure epoxides and diols which are important and versatile synthetic intermediates for the fine chemical and pharmaceutical industries. Despite these benefits, ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2020.109592

    authors: Stojanovski G,Dobrijevic D,Hailes HC,Ward JM

    更新日期:2020-09-01 00:00:00

  • The use of oxygen uptake rate measurements to control the supply of toxic substrate: toluene hydroxylation by Pseudomonas putida UV4.

    abstract::During toluene hydroxylation, catalyzed by Pseudomonas putida UV4 one molecule of oxygen is added to the aromatic ring to produce the dihydroxylated (non-aromatic) ring structure, toluene cis-glycol. Toluene, which is toxic to the cells at aqueous phase concentration above ( approximately 2.4 mmol), is fed to the reac...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(00)00289-1

    authors: Carragher JM,McClean WS,Woodley JM,Hack CJ

    更新日期:2001-02-01 00:00:00

  • Production of d-glucuronic acid from myo-inositol using Escherichia coli whole-cell biocatalyst overexpressing a novel myo-inositol oxygenase from Thermothelomyces thermophile.

    abstract::D-glucuronic acid (GlcUA) is an important intermediate with numerous applications in the food, cosmetics, and pharmaceutical industries. Its biological production routes which employ myo-inositol oxygenase (MIOX) as the key enzyme are attractive. In this study, five diverse MIOX-encoding genes, from Cryptococcus neofo...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2019.04.013

    authors: Teng F,You R,Hu M,Liu W,Wang L,Tao Y

    更新日期:2019-08-01 00:00:00

  • Engineering and optimization of phosphate-responsive phytase expression in Pichia pastoris yeast for phytate hydrolysis.

    abstract::Phytate is the major storage form of phosphorus in plants. It is present in cereals and raw materials of vegetable origin used in animal and human diets. However, non-ruminant animals have little phytase activity in their guts and, therefore, cannot digest phytate. As a result, almost all dietary phytate is discharged...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2020.109533

    authors: Xie Z,Fong WP,Tsang PW

    更新日期:2020-06-01 00:00:00

  • Preparation of high activity whole cell biocatalyst by permeabilization of recombinant flocculent yeast with alcohol.

    abstract::Flocculent yeast Saccharomyces cerevisiae YF234 (MATa ura3-52 trp1Delta2 his ade 2-1 can1-100 sta1 FLO8) cells overexpressing glyoxalase I and having strong flocculation ability were permeabilized with isopropyl alcohol and ethanol under various conditions. The treatment with 40% isopropyl alcohol significantly improv...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(00)00304-5

    authors: Kondo A,Liu Y,Furuta M,Fujita Y,Matsumoto T,Fukuda H

    更新日期:2000-12-01 00:00:00

  • RNA interference with carbon catabolite repression in Trichoderma koningii for enhancing cellulase production.

    abstract::The cellulase and xylanase genes of filamentous Trichoderma fungi exist under carbon catabolite repression mediated by the regulator carbon catabolite repressor (CREI). Our objective was to find the role of CREI in a cellulase-hyperproducing mutant of Trichoderma koningii, and address whether enzyme production can be ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2013.04.007

    authors: Wang S,Liu G,Yu J,Tian S,Huang B,Xing M

    更新日期:2013-07-10 00:00:00

  • Production of resveratrol from p-coumaric acid in recombinant Saccharomyces cerevisiae expressing 4-coumarate:coenzyme A ligase and stilbene synthase genes.

    abstract::Resveratrol is a well-known polyphenol present in red wine and exerts antioxidative and anti-carcinogenic effects on the human body. To produce resveratrol in a food-grade yeast, the 4-coumarate:coenzyme A ligase gene (4CL1) from Arabidopsis thaliana and stilbene synthase gene (STS) from Arachis hypogaea were cloned a...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2010.09.004

    authors: Shin SY,Han NS,Park YC,Kim MD,Seo JH

    更新日期:2011-01-05 00:00:00

  • Identification of a laccase from Ganoderma lucidum CBS 229.93 having potential for enhancing cellulase catalyzed lignocellulose degradation.

    abstract::Based on a differential pre-screening of 44 white-rot fungi on a lignocellulose-supplemented minimal medium, four basidiomycetes were selected for further study: Ganoderma lucidum, Polyporus brumalis, Polyporus ciliatus and Trametes versicolor. Only G. lucidum was able to grow vividly on malt extract or minimal media ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2013.08.003

    authors: Sitarz AK,Mikkelsen JD,Højrup P,Meyer AS

    更新日期:2013-12-10 00:00:00

  • Magnetosomes extracted from Magnetospirillum magneticum strain AMB-1 showed enhanced peroxidase-like activity under visible-light irradiation.

    abstract::Magnetosomes are intracellular structures produced by magnetotactic bacteria and are magnetic nanoparticles surrounded by a lipid bilayer membrane. Magnetosomes reportedly possess intrinsic enzyme mimetic activity similar to that found in horseradish peroxidase (HRP) and can scavenge reactive oxygen species depending ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2015.02.009

    authors: Li K,Chen C,Chen C,Wang Y,Wei Z,Pan W,Song T

    更新日期:2015-05-01 00:00:00

  • Discovery and characterization of new O-methyltransferase from the genome of the lignin-degrading fungus Phanerochaete chrysosporium for enhanced lignin degradation.

    abstract::Using bioinformatic homology search tools, this study utilized sequence phylogeny, gene organization and conserved motifs to identify members of the family of O-methyltransferases from lignin-degrading fungus Phanerochaete chrysosporium. The heterologous expression and characterization of O-methyltransferases from P. ...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2015.08.016

    authors: Thanh Mai Pham L,Kim YH

    更新日期:2016-01-01 00:00:00

  • Sucrose hydrolysis by thermostable immobilized inulinases from aspergillus ficuum.

    abstract::The possibility of using thermostable inulinases from Aspergillus ficuum in place of invertase for sucrose hydrolysis was explored. The commercial inulinases preparation was immobilized onto porous glass beads by covalent coupling using activation by a silane reagent and glutaraldehyde before adding the enzyme. The im...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(00)00342-2

    authors: Ettalibi M,Baratti JC

    更新日期:2001-05-07 00:00:00

  • Stabilization of Penicillium occitanis cellulases by spray drying in presence of Maltodextrin.

    abstract::The stabilization of fungal cellulases by spray drying, the thermal stability of Penicillium occitanis cellulases and the effect of some additives were studied. We observed that CMCase activity presents a good stability at 50 degrees C, even after 60 h of incubation. On the other hand, beta-glucosidase activity was mo...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(00)00322-7

    authors: Belghith H,Ellouz Chaabouni S,Gargouri A

    更新日期:2001-02-01 00:00:00

  • Effect of immobilization on the activity of rat hepatic microsomal cytochrome P450 enzymes.

    abstract::Cytochrome P450 enzyme preparations were obtained from phenobarbital-treated rats. On immobilization in Romicon PM 10 polysulfone anisotropic hollow fibers, 20-25% of the original activity remained. The immobilization procedure did not significantly alter the Km of the preparations when 7-ethoxycoumarin was the substr...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/0141-0229(93)90031-v

    authors: Fernandez-Salguero P,Gutierrez-Merino C,Bunch AW

    更新日期:1993-02-01 00:00:00

  • An efficient in vitro refolding of recombinant bacterial laccase in Escherichia coli.

    abstract::Laccases (benzenediol oxygen oxidoreductases, EC 1.10.3.2) are important multicopper enzymes that are used in many biotechnological processes. A recombinant form of laccase from Bacillus sp. HR03 was overexpressed in Escherichia coli BL-21(DE3). Inclusion body (IB) formation happens quite often during recombinant prot...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2013.03.006

    authors: Mollania N,Khajeh K,Ranjbar B,Rashno F,Akbari N,Fathi-Roudsari M

    更新日期:2013-05-10 00:00:00

  • Trypsin inactivation by latex fabricated gold nanoparticles: A new strategy towards insect control.

    abstract::Before applying nanotechnologies in biomedical and environmental areas it is advised to study interactions of nanoparticles and other nanomaterials with biomacromolecule present in living system. Moreover there is scarcity of reports on interactions between nanoparticles and biomaterials. In present report a rapid, ec...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2016.06.005

    authors: Patil CD,Borase HP,Suryawanshi RK,Patil SV

    更新日期:2016-10-01 00:00:00

  • Operational stabilities of different chemical derivatives of Novozym 435 in an alcoholysis reaction.

    abstract::Industrial use of Novozym 435 in synthesis of structured lipids and biodiesel via alcoholysis is limited by mass transfer effects of the glycerides through immobilized enzymes and its low operational stability under operation conditions. To better understand this, differently modified Novozym 435 preparations, differi...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2016.04.007

    authors: Villalba M,Verdasco-Martín CM,Dos Santos JC,Fernandez-Lafuente R,Otero C

    更新日期:2016-08-01 00:00:00

  • Multiple lignin peroxidases of Phanerochaete chrysosporium INA-12.

    abstract::Nine proteins with lignin peroxidase activity were separated from cultures of Phanerochaete chrysosporium INA-12 in glycerol as carbon source and non-nitrogen limited. Four lignin peroxidase isozymes (4, 5, 8, 9) were purified and characterized. Although differences in kinetic parameters could be shown, antibody react...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/0141-0229(90)90056-v

    authors: Odier E,Delattre M

    更新日期:1990-06-01 00:00:00

  • CAH1 and CAH2 as key enzymes required for high bicarbonate tolerance of a novel microalga Dunaliella salina HTBS.

    abstract::Outdoor microalgal cultivation with high concentration bicarbonate has been considered as a strategy for reducing contamination and improving carbon supply efficiency. The mechanism responsible for algae's strong tolerance to high bicarbonate however, remains not clear. In this study, we isolated and characterized a s...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2016.02.010

    authors: Hou Y,Liu Z,Zhao Y,Chen S,Zheng Y,Chen F

    更新日期:2016-06-01 00:00:00

  • A quenched-flow system for measuring heterogeneous enzyme kinetics with sub-second time resolution.

    abstract::Even though many enzyme processes occur at the interface of an insoluble substrate, these reactions are generally much less studied than homogenous enzyme reactions in the aqueous bulk. Interfacial (or heterogeneous) enzyme reactions involve several reaction steps, and the established experimental approach to elucidat...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2017.06.009

    authors: Olsen JP,Kari J,Borch K,Westh P

    更新日期:2017-10-01 00:00:00

  • Effects of growth medium composition, iron sources and atmospheric oxygen concentrations on production of luciferase-bacterial magnetic particle complex by a recombinant Magnetospirillum magneticum AMB-1.

    abstract::Growth conditions for mass production of luciferase-bacterial magnetic particles (BMPs) by a recombinant Magnetospirillum magneticum AMB-1 were investigated in a pH-regulated fed-batch culture system. Enrichment of growth medium with L-cysteine, yeast extract and polypeptone enhanced both bacterial growth and BMP prod...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/s0141-0229(01)00343-x

    authors: Yang C,Takeyama H,Tanaka T,Matsunaga T

    更新日期:2001-07-05 00:00:00

  • Production of glutaric acid from 5-aminovaleric acid using Escherichia coli whole cell bio-catalyst overexpressing GabTD from Bacillus subtilis.

    abstract::Glutaric acid is one of the promising C5 platform compounds in the biochemical industry. It can be produced chemically, through the ring-opening of butyrolactone followed by hydrolysis. Alternatively, glutaric acid can be produced via lysine degradation pathways by microorganisms. In microorganisms, the overexpression...

    journal_title:Enzyme and microbial technology

    pub_type: 杂志文章

    doi:10.1016/j.enzmictec.2018.07.002

    authors: Hong YG,Moon YM,Hong JW,No SY,Choi TR,Jung HR,Yang SY,Bhatia SK,Ahn JO,Park KM,Yang YH

    更新日期:2018-11-01 00:00:00