Chemistry:Nourseothricin
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| 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
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C19H34N8O8 | |
| Molar mass | 502.529 g·mol−1 |
| ~ 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]
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
NTC is highly soluble in water (~ 1 g/mL) and stable in solution for 2 years at 4 °C.[6]
References
- ↑ "Nourseothricin". http://www.jenabioscience.com/images/741d0cd7d0/NTC-Flyer.pdf.
- ↑ "Nourseothricin N-acetyl transferase: a positive selection marker for mammalian cells". PLOS ONE 8 (7): e68509. 2013. doi:10.1371/journal.pone.0068509. PMID 23861913. Bibcode: 2013PLoSO...868509K.
- ↑ Morgan, Christopher E.; Kang, Yoon-Suk; Green, Alex B.; Smith, Kenneth P.; Dowgiallo, Matthew G.; Miller, Brandon C.; Chiaraviglio, Lucius; Truelson, Katherine A. et al. (2023-05-16). "Streptothricin F is a bactericidal antibiotic effective against highly drug-resistant gram-negative bacteria that interacts with the 30S subunit of the 70S ribosome" (in en). PLOS Biology 21 (5): e3002091. doi:10.1371/journal.pbio.3002091. ISSN 1545-7885. PMID 37192172.
- ↑ "Sequence and transcriptional analysis of the nourseothricin acetyltransferase-encoding gene nat1 from Streptomyces noursei". Gene 127 (1): 127–31. 1993. doi:10.1016/0378-1119(93)90627-f. PMID 8486278.
- ↑ "CaNAT1, a heterologous dominant selectable marker for transformation of Candida albicans and other pathogenic Candida species". Infection and Immunity 73 (2): 1239–42. 2005. doi:10.1128/IAI.73.2.1239-1242.2005. PMID 1566497.
- ↑ NTC properties, Jena Bioscience
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