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6-Aminopenicillanic acid

$64

  • Brand : BIOFRON

  • Catalogue Number : BN-O1163

  • Specification : 98%(HPLC)

  • CAS number : 551-16-6

  • Formula : C8H12N2O3S

  • Molecular Weight : 216.26

  • PUBCHEM ID : 11082

  • Volume : 5mg

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Catalogue Number

BN-O1163

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

216.26

Appearance

Botanical Source

Structure Type

Category

SMILES

CC1(C(N2C(S1)C(C2=O)N)C(=O)O)C

Synonyms

[2S-(2a,5a,6b)]-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid/6-aps/6-AMINO PENICILLINIC ACID/6-Aminopenicillanic acid/penicin/6-Aminopenicillansure/4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-/aminopenicillanicacid/6-APA/6b-Aminopenicillanic Acid/(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid/Amoxicillin Impurity 1

IUPAC Name

(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Density

1.5±0.1 g/cm3

Solubility

Flash Point

232.1±28.7 °C

Boiling Point

460.2±45.0 °C at 760 mmHg

Melting Point

198-200 °C (dec.)(lit.)

InChl

InChl Key

NGHVIOIJCVXTGV-ALEPSDHESA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:551-16-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29614323

Abstract

Aqueous two-phase systems (ATPSs) were screened for the production of 6-aminopenicillanic acid (6-APA) catalyzed by penicillin acylase, followed by the extractive separation of 6-APA from the reaction mixture. The key point of this study was to find an ATPS exhibiting a large difference in the partition coefficients of the biocatalyst and reaction products. Several ATPSs based on polyethylene glycol (PEG)/phosphate, PEG/citrate, and PEG/dextran were tested. We found that an ATPS consisting of 15 wt% of PEG 4000, 10 wt% of phosphates, 75 wt% of water (pH value 8.0 after dissolution) provided optimal separation of 6-APA from the enzyme. While the 6-APA was mainly found in the top PEG phase, the free enzyme favored the bottom salt-rich phase. This ATPS also fulfils other important requirements: (i) high buffering capacity, reducing an undesirable pH decrease due to the dissociation of phenylacetic acid (the side product of the reaction), (ii) a relatively low cost of the ATPS components, (iii) the possibility of electrophoretic transport of fine droplets as well as the reaction products for both the acceleration of phase separation and the enhancement of 6-APA concentration in the product stream. Extraction experiments in microcapillary and batch systems showed that the transport of 6-APA formed in the salt-rich phase to the corresponding PEG phase could occur within 30 s. The experimental results described form a base of knowledge for the development of continuously operating integrated microfluidic reactors-separators driven by an electric field for the efficient production of 6-APA.

KEYWORDS

6-aminopenicillanic acid; Aqueous two-phase systems; Extraction; Microchip; Microreactor; Penicillin acylase.

Title

Optimization of Aqueous Two-Phase Systems for the Production of 6-aminopenicillanic Acid in Integrated Microfluidic Reactors-Separators

Author

Lucie Vobecka 1, Alexandr Romanov 2, Zdeněk Slouka 3, Pavel Hasal 4, Michal Přibyl 5

Publish date

2018 Dec 25

PMID

30243389

Abstract

Penicillin acylase is commonly used to produce the medical intermediates of 6-Aminopenicillanic acid (6-APA) and 7-Aminodesacetoxycephalosporanic acid (7-ADCA) in industrial process. Nowadays, Penicillin G acylase (PGA) has been widely applied for making pharmaceutical intermediates, while penicillin V acylase (PVA) has been less used for that due to its low activity and poor conversion. In this study, a PVA from Bacillus sphaericus (BspPVA) was employed for directed evolution study with hoping to increase its catalytic efficiency. Finally, a triple mutant BspPVA-3 (T63S/N198Y/S110C) was obtained with 12.4-fold specific activity and 11.3-fold catalytic efficiency higher than BspPVA-wt (wild type of BspPVA). Moreover, the conversion yields of 6-APA catalyzed by BspPVA-3 reached 98% with 20% (w/v) penicillin V as substrate, which was significantly higher than that of the BspPVA-wt (85%). Based on the analysis of modeling, the enhancement of specific activity of mutant BspPVA-3 was probably attributed to the changes in the number of hydrogen bonds within the molecules. The triple mutant PVA developed in this study has a potential for large-scale industrial application for 6-APA production.

KEYWORDS

6-APA; Bacillus sphaericus; Directed evolution; Penicillin V acylase (PVA).

Title

Directed Evolution of a Penicillin V Acylase From Bacillus Sphaericus to Improve Its Catalytic Efficiency for 6-APA Production

Author

Gang Xu 1, Qiang Zhao 2, Bin Huang 2, Jinghui Zhou 2, Fuxiang Cao 3

Publish date

2018 Dec;

PMID

26852849

Abstract

In an effort to promote sustainability and to reduce manufacturing costs, the traditional production process for 6-aminopenicillanic acid (6-APA) has been modified to include less processing units. The objectives of this study are to investigate the degradation kinetics of 6-APA, to propose a reasonable degradation mechanism, and to optimize the manufacturing conditions within this new process. A series of degradation kinetic studies were conducted in the presence of impurities, as well as at various chemical and physical conditions. The concentrations of 6-APA were determined by high-performance liquid chromatography. An Arrhenius-type kinetic model was established to give a more accurate prediction on the degradation rates of 6-APA. A hydrolysis degradation mechanism is shown to be the major pathway for 6-APA. The degradation mechanisms and the kinetic models for 6-APA in the new system enable the design of a good manufacturing process with optimized parameters

KEYWORDS

chemical stability; degradation products; kinetics; processing; unit operations.

Title

Degradation Kinetics and Mechanism of a β-Lactam Antibiotic Intermediate, 6-Aminopenicillanic Acid, in a New Integrated Production Process

Author

Min Su 1, Hua Sun 2, Yingying Zhao 3, Aidang Lu 4, Xiaohui Cao 5, Jingkang Wang 6

Publish date

2016 Jan;


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