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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:57869 ;
ChemSpider	10611 ;
ECHA InfoCard	100.008.177
EC Number	208-993-4;
PubChem CID	11082;
UNII	QR0C4R7XVN ;
CompTox Dashboard (EPA)	DTXSID7046097 ;
	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	216.26 g·mol−1
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 [77 °F], 100 kPa).
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	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

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

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[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.