Surf Wiki
Save to docs
general/beta-lactam-antibiotics

From Surf Wiki (app.surf) — the open knowledge base

6-APA

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.

The semi-synthetic penicillins derived from 6-APA are also referred to as penicillins and are considered part of the penicillin family of antibiotics.

History

In 1958, Beecham scientists from Brockham Park, Surrey, found a way to obtain 6-APA from penicillin. Other β-lactam antibiotics could then be synthesized by attaching various side-chains to the nucleus. 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

References

  1. (2014). "Enzymatic hydrolysis of penicillin and in situ product separation in thermally induced reversible phase-separation of ionic liquids/Water mixture". Enzyme and Microbial Technology.
  2. (2017). "Medicinal Chemistry". Oxford University Press.
  3. (1959). "Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations". Nature.
  4. 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.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

beta-lactam-antibiotics sulfur-heterocycles amines
Want to explore this topic further?

Ask Mako anything about 6-APA — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report