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551-16-6 | 6-Aminopenicillanic acid
CAS No: 551-16-6 Catalog No: AG0034BO MDL No:MFCD00005176
Product Description
Catalog Number:
AG0034BO
Chemical Name:
6-Aminopenicillanic acid
CAS Number:
551-16-6
Molecular Formula:
C8H12N2O3S
Molecular Weight:
216.2575
MDL Number:
MFCD00005176
IUPAC Name:
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChI:
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChI Key:
NGHVIOIJCVXTGV-ALEPSDHESA-N
SMILES:
OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N
EC Number:
208-993-4
UNII:
QR0C4R7XVN
Properties
Complexity:
318
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
216.057g/mol
Formal Charge:
0
Heavy Atom Count:
14
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
216.255g/mol
Monoisotopic Mass:
216.057g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
109A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.1
Literature
| Title | Journal |
|---|---|
| Penicillin inhibitors of purple acid phosphatase. | Bioorganic & medicinal chemistry letters 20120401 |
| Improving the diastereoselectivity of penicillin G acylase for ampicillin synthesis from racemic substrates. | Protein engineering, design & selection : PEDS 20120301 |
| A peptidoglycan fragment triggers β-lactam resistance in Bacillus licheniformis. | PLoS pathogens 20120301 |
| Crystallization and X-ray structure analysis of a thermostable penicillin G acylase from Alcaligenes faecalis. | Acta crystallographica. Section F, Structural biology and crystallization communications 20120301 |
| Binding of β-lactam antibiotics to a bioinspired dizinc complex reminiscent of the active site of metallo-β-lactamases. | Inorganic chemistry 20120220 |
| Proteomics shows new faces for the old penicillin producer Penicillium chrysogenum. | Journal of biomedicine & biotechnology 20120101 |
| Enzymatic synthesis of ampicillin: nonlinear modeling, kinetics estimation, and adaptive control. | Journal of biomedicine & biotechnology 20120101 |
| Quorum quenching revisited--from signal decays to signalling confusion. | Sensors (Basel, Switzerland) 20120101 |
| Improved X-ray diffraction from Bacillus megaterium penicillin G acylase crystals through long cryosoaking dehydration. | Acta crystallographica. Section F, Structural biology and crystallization communications 20111201 |
| Ionization constants and solubility of compounds involved in enzymatic synthesis of aminopenicillins and aminocephalosporins. | Bioprocess and biosystems engineering 20111101 |
| Characteristic features and biotechnological applications of cross-linked enzyme aggregates (CLEAs). | Applied microbiology and biotechnology 20111101 |
| [Determination of penicillin intermediate and three penicillins in milk by high performance capillary electrophoresis]. | Se pu = Chinese journal of chromatography 20111101 |
| Effect of internal diffusional restrictions on the hydrolysis of penicillin G: reactor performance and specific productivity of 6-APA with immobilized penicillin acylase. | Applied biochemistry and biotechnology 20110901 |
| [Four recurrences of acute generalized exanthematous pustulosis (AGEP) with three different drugs in the same patient]. | Annales de dermatologie et de venereologie 20110501 |
| Comparative study of 6-APA production by free and agar immobilized bacteria in nutrient broth culture. | Indian journal of experimental biology 20110401 |
| Performance and model of a full-scale up-flow anaerobic sludge blanket (UASB) to treat the pharmaceutical wastewater containing 6-APA and amoxicillin. | Journal of hazardous materials 20110130 |
| Immobilization of penicillin G acylase on macro-mesoporous silica spheres. | Bioresource technology 20110101 |
| The genome sequence of E. coli W (ATCC 9637): comparative genome analysis and an improved genome-scale reconstruction of E. coli. | BMC genomics 20110101 |
| Degeneration of penicillin production in ethanol-limited chemostat cultivations of Penicillium chrysogenum: A systems biology approach. | BMC systems biology 20110101 |
| [Research for the improvement of acylation conditions in antistaphylococcal penicillin synthesis]. | Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi 20110101 |
| One-pot, two-step enzymatic synthesis of amoxicillin by complexing with Zn2+. | Applied microbiology and biotechnology 20100901 |
| Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study. | Bioprocess and biosystems engineering 20100601 |
| Immobilized aculeacin A acylase from Actinoplanes utahensis: characterization of a novel biocatalyst. | Bioresource technology 20100601 |
| A process to produce penicillin G acylase by surface-adhesion fermentation using Mucor griseocyanus to obtain 6-aminopenicillanic acid by penicillin G hydrolysis. | Applied biochemistry and biotechnology 20100401 |
| Enzymatic synthesis of amoxicillin via a one-pot enzymatic hydrolysis and condensation cascade process in the presence of organic co-solvents. | Applied biochemistry and biotechnology 20100401 |
| Improved A. faecalis penicillin amidase mutant retains the thermodynamic and pH stability of the wild type enzyme. | The protein journal 20100401 |
| FT-IR, FT-Raman, ab initio and DFT structural and vibrational frequency analysis of 6-aminopenicillanic acid. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100101 |
| Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase. | Preparative biochemistry & biotechnology 20100101 |
| Heterologous expression of leader-less pga gene in Pichia pastoris: intracellular production of prokaryotic enzyme. | BMC biotechnology 20100101 |
| Covalent anchoring of chloroperoxidase and glucose oxidase on the mesoporous molecular sieve SBA-15. | International journal of molecular sciences 20100101 |
| In vitro and in vivo comparison of the anti-staphylococcal efficacy of generic products and the innovator of oxacillin. | BMC infectious diseases 20100101 |
| Acute generalized exanthematous pustulosis (AGEP) induced by terbinafine and two different antibiotics: four recurrences. | European journal of dermatology : EJD 20100101 |
| Use of enzymes in the production of semi-synthetic penicillins and cephalosporins: drawbacks and perspectives. | Current medicinal chemistry 20100101 |
| Protein engineering of penicillin acylase. | Acta naturae 20100101 |
| Rhodotorula aurantiaca penicillin V acylase: active site characterization and fluorometric studies. | Journal of photochemistry and photobiology. B, Biology 20091109 |
| Mutation of Residue βF71 of Escherichia coli Penicillin Acylase Results in Enhanced Enantioselectivity and Improved Catalytic Properties. | Acta naturae 20091001 |
| Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase. | Bioorganic & medicinal chemistry letters 20090715 |
| Human health risk assessment of penicillin/aminopenicillin resistance in enterococci due to penicillin use in food animals. | Risk analysis : an official publication of the Society for Risk Analysis 20090601 |
| Hypersensitivity reactions to penicillins: studies in a group of patients with negative benzylpenicillin G skin test. | Journal of clinical pharmacy and therapeutics 20090601 |
| Small molecule inhibition of a Group II chaperonin: pinpointing a loop region within the equatorial domain as necessary for protein refolding. | Archives of biochemistry and biophysics 20090101 |
| Molecular characterization of a fungal gene paralogue of the penicillin penDE gene of Penicillium chrysogenum. | BMC microbiology 20090101 |
| An engineered yeast efficiently secreting penicillin. | PloS one 20090101 |
| Free-radical destruction of beta-lactam antibiotics in aqueous solution. | The journal of physical chemistry. A 20080814 |
| Hydrogel coated monoliths for enzymatic hydrolysis of penicillin G. | Journal of industrial microbiology & biotechnology 20080801 |
| Poststreptococcal dystonia with bilateral striatal enlargement: MR imaging and spectroscopic findings. | AJNR. American journal of neuroradiology 20080801 |
| Fluorophore-labeled beta-lactamase as a biosensor for beta-lactam antibiotics: a study of the biosensing process. | Journal of the American Chemical Society 20080521 |
| Quantitative analysis of metabolites in complex biological samples using ion-pair reversed-phase liquid chromatography-isotope dilution tandem mass spectrometry. | Journal of chromatography. A 20080411 |
| Development of the semi-synthetic penicillins and cephalosporins. | International journal of antimicrobial agents 20080301 |
| [Phase transfer catalyzed bioconversion of penicillin G to 6-APA by immobilized penicillin acylase in recyclable aqueous two-phase systems with light/pH sensitive copolymers]. | Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20080301 |
| Enzymatic hydrolysis of penicillin for 6-APA production in three-liquid-phase system. | Applied biochemistry and biotechnology 20080201 |
| Saturation mutagenesis reveals the importance of residues alphaR145 and alphaF146 of penicillin acylase in the synthesis of beta-lactam antibiotics. | Journal of biotechnology 20080101 |
| [Etiology of urinary tract infections and antimicrobial susceptibility: a study conducted on a population of children hospitalized in the Department of Pediatrics at Warsaw Bielany Hospital; 2004-2006]. | Medycyna wieku rozwojowego 20080101 |
| Antibacterial and toxicological evaluation of beta-lactams synthesized by immobilized beta-lactamase-free penicillin amidase produced by Alcaligenes sp. | Indian journal of experimental biology 20071201 |
| Calixarenes in a membrane environment: a monolayer study on the miscibility of three p-tert-butylcalix[4]arene beta-lactam derivatives with 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine. | The journal of physical chemistry. B 20071122 |
| Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants. | Pakistan journal of biological sciences : PJBS 20071101 |
| 6-aminopenicillanic acid production by intact cells of E. coli containing penicillin G acylase (PGA). | Pakistan journal of biological sciences : PJBS 20070915 |
| Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20070901 |
| In vivo transport of the intermediates of the penicillin biosynthetic pathway in tailored strains of Penicillium chrysogenum. | Applied microbiology and biotechnology 20070801 |
| Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays. | Analytical chemistry 20070701 |
| Molecular cloning and characterization of thermostable beta-lactam acylase with broad substrate specificity from Bacillus badius. | Journal of bioscience and bioengineering 20070501 |
| Association of IL-10 level and IL-10 promoter SNPs with specific antibodies in penicillin-allergic patients. | European journal of clinical pharmacology 20070301 |
| The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA). | International journal of antimicrobial agents 20070101 |
| Application of cross-linked enzyme aggregates of Bacillus badius penicillin G acylase for the production of 6-aminopenicillanic acid. | Letters in applied microbiology 20070101 |
| Enzymatic hydrolysis of penicillin in mixed ionic liquids/water two-phase system. | Biotechnology progress 20070101 |
| [Microspeciation of amphoteric molecules of unusual acid-base properties]. | Acta pharmaceutica Hungarica 20070101 |
| Penicillin acylase catalysis in the presence of ionic liquids. | Bioprocess and biosystems engineering 20061201 |
| Immobilization of permeabilized whole cell penicillin G acylase from Alcaligenes faecalis using pore matrix crosslinked with glutaraldehyde. | Biotechnology letters 20060701 |
| Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays. | Analytical chemistry 20060315 |
| [Modulatory effect of antimicrobial agents or aminoacids on the oxidative burst of polymorphonuclear neutrophils triggered by formylmethionyl-leucyl-phenylalanine (fMLP)]. | Pathologie-biologie 20060201 |
| Erythema multiforme to amoxicillin with concurrent infection by Epstein-Barr virus. | Allergologia et immunopathologia 20060101 |
| High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium. | Microbial cell factories 20060101 |
| UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria). | The Journal of biological chemistry 20051202 |
| Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics. | Journal of agricultural and food chemistry 20050824 |
| Reactions of pyrazolylborate-zinc-hydroxide complexes related to beta-lactamase activity. | Inorganic chemistry 20050613 |
| [Disseminated actinomycosis]. | Revue des maladies respiratoires 20050601 |
| Purification and characterization of inducible cephalexin synthesizing enzyme in Gluconobacter oxydans. | Bioscience, biotechnology, and biochemistry 20050301 |
| Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20050101 |
| Evidence for the involvement of arginyl residue at the active site of penicillin G acylase from Kluyvera citrophila. | Biotechnology letters 20041001 |
| Purification, substrate specificity, and N-terminal amino acid sequence analysis of a beta-lactamase-free penicillin amidase from Alcaligenes sp. | Applied microbiology and biotechnology 20040801 |
| Increasing the synthetic performance of penicillin acylase PAS2 by structure-inspired semi-random mutagenesis. | Protein engineering, design & selection : PEDS 20040701 |
| Modifying the substrate specificity of penicillin G acylase to cephalosporin acylase by mutating active-site residues. | Biochemical and biophysical research communications 20040625 |
| [Treatment mostly not in line with current knowledge. New guidelines for sinusitis therapy]. | MMW Fortschritte der Medizin 20040610 |
| Chromophoric spin-labeled beta-lactam antibiotics for ENDOR structural characterization of reaction intermediates of class A and class C beta-lactamases. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20040501 |
| Penicillin G acylase-based stationary phases: analytical applications. | Journal of pharmaceutical and biomedical analysis 20040416 |
| Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation. | Plant cell reports 20040401 |
| Penicillin acylase-catalyzed synthesis of beta-lactam antibiotics in highly condensed aqueous systems: beneficial impact of kinetic substrate supersaturation. | Biotechnology and bioengineering 20040205 |
| Production of 6-aminopenicillanic acid in aqueous two-phase systems by recombinant Escherichia coli with intracellular penicillin acylase. | Biotechnology letters 20040101 |
| Recent biotechnological interventions for developing improved penicillin G acylases. | Journal of bioscience and bioengineering 20040101 |
| Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients. | Chinese medical journal 20031201 |
| Isolation and characterization of a new strain of Achromobacter sp. with beta-lactam antibiotic acylase activity. | Applied microbiology and biotechnology 20031001 |
| Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of beta-lactam antibiotics. | European journal of biochemistry 20030901 |
| Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: p-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis. | Biotechnology and applied biochemistry 20030801 |
| A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity. | Journal of microbiological methods 20030701 |
| Industrial production of beta-lactam antibiotics. | Applied microbiology and biotechnology 20030601 |
| Study of nucleophile binding in the penicillin acylase active center. Kinetic analysis. | Biochemistry. Biokhimiia 20030301 |
| Continuous penicillin G hydrolysis in an electro-membrane reactor with immobilized penicillin G acylase. | Biotechnology letters 20030301 |
| Biotechnological applications of penicillin acylases: state-of-the-art. | Applied microbiology and biotechnology 20030101 |
| Adsorption of components of enzymatic synthesis of ampicillin on different hydrophobic resins. | Applied biochemistry and biotechnology 20030101 |
| Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents. | Biotechnology progress 20030101 |
| Enzymatic synthesis of amoxicillin: avoiding limitations of the mechanistic approach for reaction kinetics. | Biotechnology and bioengineering 20021220 |
| Monitoring of ampicillin and its related substances by NMR. | Journal of pharmaceutical and biomedical analysis 20021107 |
| beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20021101 |
| Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions. | Biochimica et biophysica acta 20020923 |
| Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry. | Journal of pharmaceutical and biomedical analysis 20020701 |
| Role of alphaArg145 and betaArg263 in the active site of penicillin acylase of Escherichia coli. | The Biochemical journal 20020701 |
| Penicillin acylase-catalyzed ampicillin synthesis using a pH gradient: a new approach to optimization. | Biotechnology and bioengineering 20020605 |
| Equilibrium modeling of extractive enzymatic hydrolysis of penicillin G with concomitant 6-aminopenicillanic acid crystallization. | Biotechnology and bioengineering 20020520 |
| The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase. | European journal of biochemistry 20020401 |
| Activity coefficients of antibiotics in aqueous NaCl solutions at 298.2 K. | Biophysical chemistry 20020219 |
| Comparison of aqueous and nonaqueous carrier electrolytes for the separation of penicillin V and related substances by capillary electrophoresis with UV and mass spectrometric detection. | Electrophoresis 20020201 |
| [Penicillin G acylase--synthesis, regulation, production]. | Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20020101 |
| Inoculum studies in production of penicillin G acylase by Bacillus megaterium ATCC 14945. | Applied biochemistry and biotechnology 20020101 |
| A novel enzyme reactor using gluten membrane entrapping cell-associated enzyme. | Biotechnology and bioengineering 20011201 |
| The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography. | Electrophoresis 20011001 |
| Physiological characterisation of Penicillium chrysogenum strains expressing the expandase gene from Streptomyces clavuligerus during batch cultivations. Growth and adipoyl-7-aminodeacetoxycephalosporanic acid production. | Applied microbiology and biotechnology 20011001 |
| Contrasting fates for 6-alpha-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS). | Bioorganic & medicinal chemistry letters 20010917 |
| Immobilized penicillin G acylase as reactor and chiral selector in liquid chromatography. | Journal of chromatography. A 20010706 |
| Highly efficient synthesis of ampicillin in an 'aqueous solution-precipitate' system: repetitive addition of substrates in a semicontinuous process. | Biotechnology and bioengineering 20010605 |
| Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. | Cellular and molecular life sciences : CMLS 20010501 |
| [Studies on the immobilized penicillin acylase on polymer beads]. | Wei sheng wu xue bao = Acta microbiologica Sinica 20010401 |
| Pyrocatechol violet in pharmaceutical analysis. Part I. A spectrophotometric method for the determination of some beta-lactam antibiotics in pure and in pharmaceutical dosage forms. | Farmaco (Societa chimica italiana : 1989) 20010301 |
| Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | Journal of molecular recognition : JMR 20010101 |
| Biotransformations catalyzed by multimeric enzymes: stabilization of tetrameric ampicillin acylase permits the optimization of ampicillin synthesis under dissociation conditions. | Biomacromolecules 20010101 |
| [Determination of degraded products of penicillin by high performance liquid chromatography]. | Se pu = Chinese journal of chromatography 20010101 |
| IgG and IgE antibodies in subjects allergic to penicillins recognize different parts of the penicillin molecule. | International archives of allergy and immunology 19970101 |
| Epitope mapping of beta-lactam antibiotics with the use of monoclonal antibodies. | Toxicology 19950331 |
| Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. | International archives of allergy and immunology 19920101 |
| Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy. | Molecular immunology 19901101 |
| IgE antibodies for penicillins and cephalosporins in rats. II. Antigenic specificity of rat anti-penicillin-OvA IgE sera. | The Journal of antibiotics 19810101 |
| Study of penicillin antibodies by fluorescence polarization and immunodiffusion. | The Journal of experimental medicine 19651130 |
| Hypersensitivity to penicillenic acid derivatives in human beings with penicillin allergy. | The Journal of experimental medicine 19620331 |
| Some immunochemical properties of penicillenic acid. An antigenic determinant derived from penicillin. | The Journal of experimental medicine 19601130 |
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