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A70909

Sigma-Aldrich

(+)-6-Aminopenicillanic acid

96%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H12N2O3S
CAS Number:
551-16-6
Molecular Weight:
216.26
Beilstein:
15080
EC Number:
208-993-4
MDL number:
MFCD00005176
UNSPSC Code:
12352005
PubChem Substance ID:
24891174
NACRES:
NA.22

Quality Level

200

Assay

96%

form

powder

optical activity

[α]22/D +276.3°, c = 1.2 in 0.1 M HCl

mp

198-200 °C (dec.) (lit.)

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O

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

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General description

(+)-6-Aminopenicillanic acid is the core moiety of different penicillins. It can be prepared from the benzylpenicillin silyl ester via cleavage of the amide bond. The coating of (+)-6-aminopenicillanic acid on silver nanoparticles (6APA-AgNPs), imparts them with an ability to detect chromium (IV) in human erythrocytes.
Chemical structure: ß-lactam

Application

(+)-6-Aminopenicillanic acid can be used as a starting material for the synthesis of (6S,7S)-cephalosporins, and organotin polyamine esters by reacting with organotin dihalides via interfacial polycondensation.
It reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.4

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Organotin polyamine esters from reaction of 6-aminopenicillanic acid and organotin dihalides
Carraher Jr CE, et al.
J. Polym. Mater., 29(4), 387-387 (2012)
6-aminopenicillanic acid.
Rolinson GN.
Chemotherapy, 2(1), 52-59 (1961)
Joanna Skiba et al.
European journal of medicinal chemistry, 57, 234-239 (2012-10-18)
We report on the synthesis of ferrocenyl-ampicillin and ferrocenyl-6-aminopenicillinic acid bioconjugates. Title compounds were characterized by (1)H NMR, IR, MS and elemental analysis. These novel ferrocenyl-antibiotic conjugates were also investigated by cyclic voltammetry (CV). Ferrocenyl-ampicillin complexes revealed reversible uncomplicated oxidation
Ye-Wang Zhang et al.
Applied microbiology and biotechnology, 88(1), 49-55 (2010-06-23)
A one-pot, two-step enzymatic synthesis of amoxicillin from penicillin G, using penicillin acylase, is presented. Immobilized penicillin acylase from Kluyvera citrophila was selected as the biocatalyst for its good pH stability and selectivity. Hydrolysis of penicillin G and synthesis of
David A Harris et al.
Bioorganic & medicinal chemistry letters, 19(14), 3787-3790 (2009-05-12)
We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo activity of the compound and use structure-activity relationship studies
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