A70909

Sigma-Aldrich

(+)-6-Aminopenicillanic acid

96%

Synonym(s):
6-APA, (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Empirical Formula (Hill Notation):
C8H12N2O3S
CAS Number:
Molecular Weight:
216.26
Beilstein/REAXYS Number:
15080
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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

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General description

Chemical structure: ß-lactam
(+)-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.

Application

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

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
An efficient nonenzymatic conversion of benzylpenicillin to 6-aminopenicillanic acid.
Weissenburger HWO and Van Der Hoeven MG.
Rec. Trav. Chim., 89(10), 1081-1084 (1970)
Chromium scavenging ability of silver nanoparticles in human erythrocytes, real samples and their effect on the catalase enzyme.
Rasheed W, et al.
New. J. Chem., 40(4), 3793-3802 (2016)
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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