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A70909 Sigma-Aldrich

(+)-6-Aminopenicillanic acid

96%

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

  • CAS Number 551-16-6

  • Empirical Formula (Hill Notation) C8H12N2O3S

  • Molecular Weight 216.26

  •  Beilstein/REAXYS Number 15080

  •  EC Number 208-993-4

  •  MDL number MFCD00005176

  •  PubChem Substance ID 24891174

  •  NACRES NA.22

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Properties

Related Categories A - K, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics by Mechanism of Action,
Quality Level   200
assay   96%
optical activity   [α]22/D +276.3°, c = 1.2 in 0.1 M HCl
mp   198-200 °C (dec.) (lit.)
Mode of action   cell wall synthesis | interferes
antibiotic activity spectrum   Gram-positive bacteria
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

Description

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

It reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.4

Packaging

10, 50 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A70909.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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