6-APA

6-Aminopenicillanic acid

Names
IUPAC name (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid
Identifiers
CAS Number	551-16-6
ChEBI	CHEBI:57869
ChemSpider	10611
EC Number	208-993-4
Jmol interactive 3D	Image
PubChem	11082
UNII	QR0C4R7XVN
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 Key: NGHVIOIJCVXTGV-ALEPSDHESA-N 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 Key: NGHVIOIJCVXTGV-ALEPSDHEBW
SMILES O=C(O)[C@@H]1N2C(=O)[C@@H](N)[C@H]2SC1(C)C
Properties
Chemical formula	C8H12N2O3S
Molar mass	216.257 g/mol
Appearance	white powder
Melting point	198 °C (388 °F; 471 K)
Boiling point	207 °C (405 °F; 480 K) decomp
Solubility in water	0.4 g/100 mL
log P	0.600
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

6-APA is the chemical compound (+)-6-aminopenicillanic acid.^[1]

Use

6-APA is the core of penicillins. It is obtained from the fermentation brew of the Penicillium mold and used as the main starting block for the preparation of numerous semisynthetic penicillins.

History

In 1958, Beecham scientists in the UK discovered the penicillin nucleus, 6-APA. From that starting material, a large number of new semisynthetic penicillins could be designed, whose activity was directed against problem infections.^[2]

References

1. Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations - F. R. Batchelor, F. P. Doyle, J. H. C. Nayler & G. N. Rolinson. Nature 183, 257-258 (24 January 1959) doi:10.1038/183257b0
2. F.P. Doyle, J.H.C. Nayler, G.N. Rolinson US Patent 2,941,995, filed July 22, 1958, granted June 21, 1960. Recovery of solid 6-aminopenicillanic acid.

External links

• US patent 2,941,995 on espacenet

See also

• 7-ACA