(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid
|Molar mass||216.257 g/mol|
|Melting point||198 °C (388 °F; 471 K)|
|Boiling point||207 °C (405 °F; 480 K) decomp|
|0.4 g/100 mL|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
6-APA is the chemical compound (+)-6-aminopenicillanic acid.
This useful compound can be made enzymatically, or chemically as follows, starting from penicillin G:
Weissenburger, H. W. O.; Van der Hoven, M. G.; Recl. Trav. Chim. Pays-Bas 1970, 89, 1081.
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.
- Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations - F. R. Batchelor, F. P. Doyle, J. H. C. Nayler & G. N. Rolinson. Nature 183, 257-258 (24 January 1959) doi:10.1038/183257b0
- 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.