6-Aminopenicillanic acid
(Synonyms: 6-氨基青霉烷酸; 6-APA) 目录号 : GC39782
An intermediate in the semisynthetic synthesis of penicillin antibiotics
Cas No.:551-16-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
6-Aminopenicillanic acid is an intermediate in the semisynthetic synthesis of penicillin antibiotics.1
1.Su, M., Sun, H., Zhao, Y., et al.Degradation kinetics and mechanism of a β-lactam antibiotic intermediate, 6-aminopenicillanic acid, in a new integrated production processJ. Pharm. Sci.105(1)139-146(2016)
| Cas No. | 551-16-6 | SDF | |
| 别名 | 6-氨基青霉烷酸; 6-APA | ||
| Canonical SMILES | [C@H]12SC([C@@H](N1C(=O)[C@H]2N)C(=O)O)(C)C | ||
| 分子式 | C8H12N2O3S | 分子量 | 216.26 |
| 溶解度 | DMSO : 1mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.6241 mL | 23.1203 mL | 46.2406 mL |
| 5 mM | 0.9248 mL | 4.6241 mL | 9.2481 mL |
| 10 mM | 0.4624 mL | 2.312 mL | 4.6241 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The 50th anniversary of the discovery of 6-Aminopenicillanic acid (6-APA)
Int J Antimicrob Agents 2007 Jan;29(1):3-8.PMID:17137753DOI:10.1016/j.ijantimicag.2006.09.003.
This year (2007) marks the 50th anniversary of [corrected] discovery of 6-Aminopenicillanic acid (6-APA), the precursor of all semi-synthetic penicillins [corrected] This review, by a scientist who played a major part in the discovery and a physician who participated in the early clinical trials of these antibiotics, tells the story of the discovery and of the early development of the beta-lactam antibiotics that revolutionised the treatment of infections.
Separation of phenyl acetic acid and 6-Aminopenicillanic acid applying aqueous two-phase systems based on copolymers and salts
Sci Rep 2021 Feb 10;11(1):3489.PMID:33568710DOI:10.1038/s41598-021-82476-x.
6-Aminopenicillanic acid (6-APA) is used for synthesis of semisynthetic antibiotics. Polymer-salt aqueous two-phase systems (ATPSs) were applied for separation of 6-APA and phenyl acetic acid (PAA), as the products of hydrolyzation reaction of Penicillin G/Penicillin V. The binodal curves of ATPS composed of a copolymer (reverse Pluronic 10R5, Pluronic L35 and PEG-ran-PPG) and a salt (Tri-sodium citrate, tri-potassium citrate, di-potassium phosphate, sodium sulphate and magnesium sulphate) were obtained. The results show that, at a fixed PPG/PEG ratio, block copolymers have larger two-phase region compared with random copolymer. After screening on the partition coefficient of PAA and 6-APA separately, Na2SO4 was selected for studying the effect of the copolymer structure and the composition of salt and copolymer on partitioning, considering higher selectivity of PAA and 6-APA. 10R5-Na2SO4 ATPS was selected as the most appropriate system for separation of 6-APA and PAA. This system was used for separation of mixture of 6-APA and PAA. The results show that selectivity was [Formula: see text] 53 and smaller in a system, containing a mixture of 6-APA and PAA. This observation can be justified by the interaction between 6-APA and PAA. Molecular interaction between these two molecules were investigated by the Flory-Huggins interaction parameter.
Improving the 6-Aminopenicillanic acid release process using vermiculite-alginate biocomposite bead on drug delivery system
Drug Dev Ind Pharm 2021 Sep;47(9):1489-1501.PMID:34806923DOI:10.1080/03639045.2021.2001492.
The present study deals with developing vermiculite (VMT)-alginate (Alg) composites with different cross-linker concentrations (CaCl2) to deliver the controlled 6-aminopenicillin acid (6-APA). The Characterization of synthesized composites was conducted by Fourier transform infrared spectroscopy (FTIR) and X-ray diffraction (XRD) analyses. Optimization attempts were explored via the response surface method (RSM) to best predict the actual amount of compound. The adsorption capacity of 6-APA onto this adsorbent was found to be 208.33 mg/g, which was higher than that for other clays. The equilibrium and Kinetic studies (chemical reaction and diffusion-based models) indicated that drug absorption on VMT-Alg is homogeneous with chemical interaction. An increase in cross-linker (CaCl2) concentration leads to improvement in the drug encapsulation efficiency while having no significant effect on loading efficiency. The in-vitro release of the pure drug shows a rapid burst release followed by 100% cumulative release within 6 h. Whereas, the synthesized drug with Alg substantially showed less release of 43% after 8 h. Release experiments revealed that the presence of the CaCl2 delayed the release of the 6-APA less than 35% after 12 h. The kinetic release of 6-APA is followed by the Korsmeyer-Peppas model based on Fick's law mechanism due to the kinetic exponent (n < 0.5). All studied composites antibacterial activity after 24 h exposure against E. Coli and S. aureus. The antibacterial activities of composites were evaluated by the halo of no growth. The results showed that the VMT-Alg-6APA composite had strong activity against Gram-positive and Gram-negative bacteria.
Process Development for 6-Aminopenicillanic acid Production Using Lentikats-Encapsulated Escherichia coli Cells Expressing Penicillin V Acylase
ACS Omega 2020 Nov 6;5(45):28972-28976.PMID:33225127DOI:10.1021/acsomega.0c02813.
Penicillin V acylase (PVA, EC 3.5.1.11) hydrolyzes the side chain of phenoxymethylpenicillin (Pen V) and finds application in the manufacture of the pharmaceutical intermediate 6-Aminopenicillanic acid (6-APA). Here, we report the scale-up of cultivation of Escherichia coli whole cells expressing a highly active PVA from Pectobacterium atrosepticum and their encapsulation in polyvinyl alcohol-poly(ethylene glycol) Lentikats hydrogels. A biocatalytic process for the hydrolysis of 2% (w/v) Pen V was set up in a 2 L reactor using the Lentikats-immobilized whole cells, with a customized setup to enable continuous downstream processing of the reaction products. The biocatalytic reaction afforded complete conversion of Pen V for 10 reaction cycles, with an overall 90% conversion up to 50 cycles. The bioprocess was further scaled up to the pilot-scale at 10 L, enabling complete conversion of Pen V to 6-APA for 10 cycles. The 6-APA and phenoxy acetic acid products were recovered from downstream processing with isolated yields of 85-90 and 87-92%, respectively. Immobilization in Lentikats beads improved the stability of the whole cells on storage, maintaining 90-100% activity and similar conversion efficiency after 3 months at 4 °C. The robust PVA biocatalyst can be employed in a continuous process to provide a sustainable route for bulk 6-APA production from Pen V.
Formation of 6-Aminopenicillanic acid, penicillins, and penicillin acylase by various fungi
Appl Microbiol 1966 Jan;14(1):98-104.PMID:5950252DOI:10.1128/am.14.1.98-104.1966.
Several penicillin-producing fungi were examined for ability to produce 6-Aminopenicillanic acid (6-APA) and penicillin acylase. 6-APA was found in corn steep liquor fermentations of Trichophyton mentagrophytes, Aspergillus ochraceous, and three strains of Penicillium sp. 6-APA was not detected in fermentations of Epidermophyton floccosum although penicillins were produced. 6-APA formed a large part of the total antibiotic production of T. mentagrophytes. The types of penicillins produced by various fungi were identified by paper chromatography, and it was found that all cultures produced benzylpenicillin. T. mentagrophytes and A. ochraceous showed increased yields of benzylpenicillin and the formation of phenoxymethylpenicillin in response to the addition to the fermentation medium of phenylacetic acid and phenoxyacetic acid, respectively. Washed mycelia of the three Penicillium spp. and two high penicillin-yielding strains of P. chrysogenum possessed penicillin acylase activity against phenoxymethylpenicillin. A. ochraceous, T. mentagrophytes, E. floccosum, and Cephalosporium sp. also had penicillin acylase activity against phenoxymethylpenicillin. Only two of the above fungi, T. mentagrophytes and E. floccosum, showed significant penicillin acylase activity against benzylpenicillin; in both cases it was very low. The acylase activity of A. ochraceous was considerably increased by culturing in the presence of phenoxyacetic acid. It is concluded that 6-APA frequently but not invariably accompanies the formation of penicillin, and that penicillin acylase activity against phenoxymethylpenicillin is present in all penicillin-producing fungi.