6-APA

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title: "6-APA" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["beta-lactam-antibiotics", "sulfur-heterocycles", "amines"] topic_path: "general/beta-lactam-antibiotics" source: "https://en.wikipedia.org/wiki/6-APA" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477225540 | Name = 6-Aminopenicillanic acid | ImageFile = 6-Aminopenicillanic acid.svg | ImageSize = 200px | ImageName = 6-Aminopenicillanic acid | ImageFile1 = 6-Aminopenicillanic acid (6-APA).gif | ImageSize1 = 200px | IUPACName = 6β-Amino-2,2-dimethylpenam-3α-carboxylic acid | SystematicName = (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 10611 | 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 | InChIKey = NGHVIOIJCVXTGV-ALEPSDHEBW | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = NGHVIOIJCVXTGV-ALEPSDHESA-N | CASNo_Ref = | CASNo = 551-16-6 | UNII_Ref = | UNII = QR0C4R7XVN | PubChem = 11082 | ChEBI_Ref = | ChEBI = 57869 | SMILES = O=C(O)[C@@H]1N2C(=O)C@@H[C@H]2SC1(C)C | RTECS = | EINECS = 208-993-4 |Section2={{Chembox Properties | Formula = | C=8 | H=12 | N=2 | O=3 | S=1 | Appearance = colourless | MeltingPtC = 198 | Solubility = 0.4 g/100 mL | LogP = 0.600 |Section3={{Chembox Structure | Dipole =

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.

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beta-lactam-antibioticssulfur-heterocyclesamines