Nourseothricin

Nourseothricin
	n=1-4
Names
	IUPAC name [(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
Identifiers
CAS Number	56089-12-4; 96736-11-7 (sulfate);
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2334879;
ChemSpider	29418395;
PubChem CID	71720685;
	InChI InChI=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 Key: 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;
Properties
Chemical formula	C19H34N8O8
Molar mass	502.529 g·mol−1
Solubility in water	~ 1 g/L
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1] 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.^[2]

Quick Facts Names, Identifiers ...

Streptothricin F is effective against highly drug-resistant gram-negative bacteria, including carbapenem-resistant E. coli.^[3]

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.^[4] NAT can thus act as an antibiotic resistance gene.^[5]

Properties