6-APA

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6-Aminopenicillanic acid
6-Aminopenicillanic acid
6-Aminopenicillanic acid (6-APA).gif
Names
Preferred IUPAC name
(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.177 Edit this at Wikidata
EC Number
  • 208-993-4
UNII
  • 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 checkY
    Key: NGHVIOIJCVXTGV-ALEPSDHESA-N checkY
  • 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
  • O=C(O)[C@@H]1N2C(=O)[C@@H](N)[C@H]2SC1(C)C
Properties
C8H12N2O3S
Molar mass 216.26 g·mol−1
Appearance colourless
Melting point 198 °C (388 °F; 471 K)
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 verify (what is checkY☒N ?)
Infobox references

6-APA is an abbreviation used for the name of the chemical compound (+)-6-aminopenicillanic acid. In 1958, Beecham scientists from Brockham Park, Surrey, found a way to obtain 6-APA from penicillin.[1] Other β-lactam antibiotics could then be synthesized by attaching various side-chains to the nucleus. [2] 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.[3]

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[edit]

  1. ^ 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.
  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.
  3. ^ Patrick GL (2017). Medicinal Chemistry (6th ed.). Oxford, UK: Oxford University Press. p. 425. ISBN 978-0198749691.