6-APA

{{chembox

| 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 = {{chemspidercite|correct|chemspider}}

| 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 = {{stdinchicite|correct|chemspider}}

| 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 = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NGHVIOIJCVXTGV-ALEPSDHESA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 551-16-6

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = QR0C4R7XVN

| PubChem = 11082

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 57869

| SMILES = O=C(O)[C@@H]1N2C(=O)[C@@H](N)[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.{{cite journal |doi=10.1016/j.enzmictec.2014.05.002 |title=Enzymatic hydrolysis of penicillin and in situ product separation in thermally induced reversible phase-separation of ionic liquids/Water mixture |date=2014 |last1=Mai |first1=Ngoc Lan |last2=Koo |first2=Yoon-Mo |journal=Enzyme and Microbial Technology |volume=63 |pages=34–38 |pmid=25039057 }}

The semi-synthetic penicillins derived from 6-APA are also referred to as penicillins and are considered part of the penicillin family of antibiotics.{{cite book | vauthors = Patrick GL | title=Medicinal Chemistry | edition=6th |date=2017 |page=425 |location=Oxford, UK |publisher=Oxford University Press |isbn=978-0198749691 }}