6-APA
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| IUPAC name
6β-Amino-2,2-dimethylpenam-3α-carboxylic acid
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| Systematic 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)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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6-APA ((+)-6-aminopenicillanic acid) is an organic compound that is used in the synthesis of β–lactam antibiotics including amoxicillin, ampicillin, oxacillin, and carbenicillin. The major commercial source of 6-APA is natural penicillin G, which contains an N-phenylacetyl substituent.[1]
The semi-synthetic penicillins derived from 6-APA are also referred to as penicillins and are considered part of the penicillin family of antibiotics.[2]
History
[edit | edit source]In 1958, Beecham scientists from Brockham Park, Surrey, found a way to obtain 6-APA from penicillin.[3] Other β-lactam antibiotics could then be synthesized by attaching various side-chains to the nucleus.[4] 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.[citation needed]
References
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- ^ 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.