Nourseothricin

{{Chembox

| ImageFile = Nourseothricin.svg

| ImageSize = 200px

| ImageCaption = n=1-4

| SystematicName =

| IUPACName = [(2R,3S,4R,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3,6-diaminohexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo = 56089-12-4

| CASNo1 = 96736-11-7

| CASNo1_Comment = (sulfate)

| ChEMBL = 2334879

| ChemSpiderID = 29418395

| PubChem = 71720685

| StdInChI=1S/C19H34N8O8/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27)/t7-,8+,9+,11+,12-,13+,14+,15+,17+/m0/s1

| StdInChIKey = NRAUADCLPJTGSF-ZPGVOIKOSA-N

| SMILES = C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)N[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)OC(=O)N)O)NC(=O)C[C@H](CCCN)N)O

}}

| Section2 = {{Chembox Properties

| C= 19|H= 34|N= 8|O= 8

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = ~ 1 g/L

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| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Nourseothricin (NTC) is a member of the streptothricin-class of aminoglycoside antibiotics produced by Streptomyces species. Chemically, NTC is a mixture of the related compounds streptothricin C, D, E, and F.{{Cite web|url=http://www.jenabioscience.com/images/741d0cd7d0/NTC-Flyer.pdf|title=Nourseothricin}} NTC inhibits protein synthesis by inducing miscoding. It is used as a selection marker for a wide range of organisms including bacteria, yeast, filamentous fungi, and plant cells. It is not known to have adverse side-effects on positively selected cells, a property cardinal to a selection drug.{{cite journal |vauthors=Kochupurakkal BS, Iglehart JD |title=Nourseothricin N-acetyl transferase: a positive selection marker for mammalian cells |journal=PLOS ONE |volume=8 |issue=7 |pages=e68509 |year=2013 |pmid=23861913 |pmc=3701686 |doi=10.1371/journal.pone.0068509 |bibcode=2013PLoSO...868509K |doi-access=free }}

Streptothricin F is effective against highly drug-resistant gram-negative bacteria, including carbapenem-resistant E. coli.{{Cite journal |last1=Morgan |first1=Christopher E. |last2=Kang |first2=Yoon-Suk |last3=Green |first3=Alex B. |last4=Smith |first4=Kenneth P. |last5=Dowgiallo |first5=Matthew G. |last6=Miller |first6=Brandon C. |last7=Chiaraviglio |first7=Lucius |last8=Truelson |first8=Katherine A. |last9=Zulauf |first9=Katelyn E. |last10=Rodriguez |first10=Shade |last11=Kang |first11=Anthony D. |last12=Manetsch |first12=Roman |last13=Yu |first13=Edward W. |last14=Kirby |first14=James E. |date=2023-05-16 |title=Streptothricin F is a bactericidal antibiotic effective against highly drug-resistant gram-negative bacteria that interacts with the 30S subunit of the 70S ribosome |journal=PLOS Biology |language=en |volume=21 |issue=5 |pages=e3002091 |doi=10.1371/journal.pbio.3002091 |pmid=37192172 |pmc=10187937 |issn=1545-7885 |doi-access=free }}

NTC can be inactivated by nourseothricin N-acetyl transferase (NAT) from Streptomyces noursei, an enzyme that acetylates the beta-amino group of the beta-lysine residue of NTC.{{cite journal |vauthors=Krügel H, Fiedler G, Smith C, Baumberg S |title=Sequence and transcriptional analysis of the nourseothricin acetyltransferase-encoding gene nat1 from Streptomyces noursei |journal=Gene |volume=127 |issue=1 |pages=127–31 |year=1993 |pmid=8486278 |doi= 10.1016/0378-1119(93)90627-f}} NAT can thus act as an antibiotic resistance gene.{{cite journal |vauthors=Shen J, Guo W, Köhler JR |title=CaNAT1, a heterologous dominant selectable marker for transformation of Candida albicans and other pathogenic Candida species |journal=Infection and Immunity|volume=73|issue=2 |pages=1239–42 |year=2005 |pmid=1566497 |doi= 10.1128/IAI.73.2.1239-1242.2005|s2cid=37895453 |doi-access=free |pmc=547112 }}