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6-APA

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6-Aminopenicillanic acid
6-Aminopenicillanic acid
Names
IUPAC name 6β-Amino-2,2-dimethylpenam-3α-carboxylic acid
Systematic IUPAC name (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.177 Edit this at Wikidata
EC Number
  • 208-993-4
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: NGHVIOIJCVXTGV-ALEPSDHEBW
SMILES
  • O=C(O)1N2C(=O)(N)2SC1(C)C
Properties
Chemical formula C8H12N2O3S
Molar mass 216.26 g·mol
Appearance colourless
Melting point 198 °C (388 °F; 471 K)
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

6-APA ((+)-6-aminopenicillanic acid) is a chemical compound used as an intermediate in the synthesis of β–lactam antibiotics. The major commercial source of 6-APA is still natural penicillin G. The semi-synthetic penicillins derived from 6-APA are also referred to as penicillins and are considered part of the penicillin family of antibiotics.

In 1958, Beecham scientists from Brockham Park, Surrey, found a way to obtain 6-APA from penicillin. Other β-lactam antibiotics could then be synthesized by attaching various side-chains to the nucleus. The reason why this was achieved so many years after the commercial development of penicillin by Howard Florey and Ernst Chain lies in the fact that penicillin itself is very susceptible to hydrolysis, so direct replacement of the side-chain was not a practical route to other β-lactam antibiotics.

References

  1. Patrick GL (2017). Medicinal Chemistry (6th ed.). Oxford, UK: Oxford University Press. p. 425. ISBN 978-0198749691.
  2. Batchelor, F. R.; Doyle, F. P.; Nayler, J. H. C.; Rolinson, G. N. (1959). "Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations". Nature. 183 (4656): 257–258. Bibcode:1959Natur.183..257B. doi:10.1038/183257b0. PMID 13622762. S2CID 4268993.
  3. 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.
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