6-Aminopenicillanic acid
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
 YesY
ChEBI  YesY
ChemSpider  YesY
EC number 208-993-4
Jmol-3D images Image
PubChem
UNII  N
Properties
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
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).
 N  (: YesY/N?)

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. ^ , 257-258 (24 January 1959)183 NatureSynthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations - F. R. Batchelor, F. P. Doyle, J. H. C. Nayler & G. N. Rolinson. 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