6-APA

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6-Aminopenicillanic acid
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
551-16-6 YesY
ChEBI CHEBI:57869 YesY
ChemSpider 10611 YesY
EC number 208-993-4
Jmol-3D images Image
PubChem 11082
Properties
C8H12N2O3S
Molar mass 216.257 g/mol
Appearance white powder
Melting point 198 °C (388 °F; 471 K)
Boiling point 207 °C (405 °F; 480 K) decomp
0.4 g/100 mL
log P 0.600
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

6-APA is the chemical compound (+)-6-aminopenicillanic acid.[1]

Use[edit]

6-APA is the core of penicillins. It is obtained from the fermentation brew of the Penicillium mold and used as the main starting block for the preparation of numerous semisynthetic penicillins.

Manufacture[edit]

This useful compound can be made enzymatically, or chemically as follows, starting from penicillin G:

6-aminopenicillanic acid synthesis.png

Weissenburger, H. W. O.; Van der Hoven, M. G.; Recl. Trav. Chim. Pays-Bas 1970, 89, 1081.

History[edit]

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.[2]

References[edit]

  1. ^ 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
  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.

External links[edit]

See also[edit]