551-16-6 Usage
Description
6-Aminopenicillanic acid, also known as 6-APA, is a penicillanic acid compound with a (6R)-amino substituent. It is the core structure in penicillins and serves as the active nucleus common to all penicillins. This white to cream fine powder is obtained from the fermentation brew of the Penicillium mold and is a crucial starting material for the development of various semisynthetic penicillins.
Uses
Used in Pharmaceutical Industry:
6-Aminopenicillanic acid is used as a main starting block for the preparation of numerous semisynthetic penicillins. It is essential in the development of new antibiotics with improved properties, such as enhanced efficacy, broader spectrum, and reduced side effects.
Used as a Pharmaceutical Intermediate:
6-Aminopenicillanic acid acts as a pharmaceutical intermediate, playing a vital role in the synthesis of various penicillin-based drugs. Its versatility allows for the modification of its structure to create a wide range of semisynthetic penicillins with different pharmacological characteristics.
Used in Antibiotics Research:
6-Aminopenicillanic acid is utilized in the research and development of new antibiotics. It serves as a foundation for exploring novel compounds with potential antibacterial properties, contributing to the fight against antibiotic resistance.
Used in Experimental Applications:
6-Aminopenicillanic acid is employed in experimental applications to study its properties and potential uses in various fields, including medicine, pharmacology, and biotechnology. This research can lead to the discovery of new applications and improvements in existing penicillin-based drugs.
Flammability and Explosibility
Nonflammable
Safety Profile
Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Purification Methods
This acid crystallises from water. [Kleppe & Stroninger J Biol Chem 254 4856 1979,Beilstein 27 III/IV 2858.]
Check Digit Verification of cas no
The CAS Registry Mumber 551-16-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 1 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 551-16:
(5*5)+(4*5)+(3*1)+(2*1)+(1*6)=56
56 % 10 = 6
So 551-16-6 is a valid CAS Registry Number.
InChI:InChI=1/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
551-16-6Relevant articles and documents
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Dennen
, p. 1273,1275 (1967)
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Torgovanova et al.
, (1975)
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Development of novel support for penicillin acylase and its application in 6-aminopenicillanic acid production
Ayakar, Sonal R.,Yadav, Ganapati D.
, (2019/07/31)
There is an ever-increasing demand for the β-lactam bulk intermediate 6-aminopenicillanic acid (6-APA) that has wide applications in the synthesis of newer generations of semisynthetic penicillins. It is commercially synthesized by biocatalytic transformation using penicillin acylase. Since the enzyme is soluble, immobilization on a solid porous support is necessary to make the catalyst recycleable and the process profitable. In this study, we developed a novel support of siliceous foam entrapped in a polymer matrix. Penicillin acylase was covalently immobilized on aminopropyl functionalized mesocellular foam silica (MCF) and was further cross-linked using glutaraldehyde without deactivation and upto 95% efficiency. The resulting biocatalyst had an activity of 1185 IU. mg?1 and demonstrated improved resistance to the substrate and product inhibition. These parameters along with improvement in pH and thermal stability enhanced 6-APA yield by 20% in beads. Intrinsic kinetic parameters were calculated from the developed rate equation to deduce enzyme catalytic mechanism.
Purification of amoxicillin trihydrate by impurity-coformer complexation in solution
Hsi, Kay Huai Ying,Concepcion, Anthony Joseph,Kenny, Meghan,Magzoub, Amna Ahmed,Myerson, Allan S.
, p. 6776 - 6781 (2013/09/02)
In this work, we demonstrated the purification of amoxicillin trihydrate (AMCT) by the formation of 4-hydroxyphenylglycine (4HPG)-coformer complex in solution. Without advanced knowledge of cocrystal formation of 4HPG, a workflow was established to choose