6-Aminopenicillanic acid

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Description

6-Aminopenicillanic acid (6-APA) is the central component of penicillin β-lactam antibiotics which are generated by Penicillium. 6-APA forms from penicillin G after being catalyzed by penicillin acylases. This compound can be used to create semi-synthetic antibiotics that are effective against non-penicillinase forming bacterium, such as Streptococcus and some Staphylococcus.

6-APA is used as precursor for antibiotic compounds ampicillin and amoxicillin. Antibiotic synthesis of 6-APA can be augmented with a supersaturated solution of nucleophiles. Other methods for enhancing effectiveness involves diminishing ionic strength in a reaction mixture along with the addition of 2-butanol. Implementing a pH gradient starting at pH 7 and reducing the pH to 6.5 near reaction completion can greatly increase reaction output.

Product Specifications
6-Aminopenicillanic acid
(+)-6-Aminopenicillanic acid

Formula: C8H12N2O3S

MW: 216.26 g/mol

Storage/Handling: Store at 4°C.

PubChem Chemical ID: 11082

6-Aminopenicillanic acid

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Catalog Number:
A-915-10
CAS Number:
551-16-6
$56.00

For research use only. Not for food, drug, household, or cosmetic use.
Availability:
2-3 Weeks
Shipping:
$14.99 Ground shipping (In continental US only.)

    Description

    6-Aminopenicillanic acid (6-APA) is the central component of penicillin β-lactam antibiotics which are generated by Penicillium. 6-APA forms from penicillin G after being catalyzed by penicillin acylases. This compound can be used to create semi-synthetic antibiotics that are effective against non-penicillinase forming bacterium, such as Streptococcus and some Staphylococcus.

    6-APA is used as precursor for antibiotic compounds ampicillin and amoxicillin. Antibiotic synthesis of 6-APA can be augmented with a supersaturated solution of nucleophiles. Other methods for enhancing effectiveness involves diminishing ionic strength in a reaction mixture along with the addition of 2-butanol. Implementing a pH gradient starting at pH 7 and reducing the pH to 6.5 near reaction completion can greatly increase reaction output.

    Product Specifications
    6-Aminopenicillanic acid
    (+)-6-Aminopenicillanic acid

    Formula: C8H12N2O3S

    MW: 216.26 g/mol

    Storage/Handling: Store at 4°C.

    PubChem Chemical ID: 11082

    Product Specifications

    Catalog ID: A-915
    CAS #: 551-16-6
    Formula: C8H12N2O3S
    MW: 216.26 g/mol
    Storage/handling: Store at 4°C.
    PubChem Chemical ID: 11082
    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
    InChIKey: NGHVIOIJCVXTGV-ALEPSDHESA-N
    SMILES: CC1(C(N2C(S1)C(C2=O)N)C(=O)O)C

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