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Nourseothricin

In today's world, Nourseothricin is a topic that generates great interest and debate in different areas. Whether in the academic, social, political or cultural field, Nourseothricin is a topic that leaves no one indifferent. Its relevance has transcended borders and has captured the attention of people of all ages and professions. In this article, we will delve into the different aspects related to Nourseothricin, analyzing its impact on today's society and exploring possible solutions or approaches to address this issue effectively. Through in-depth and objective research, we will seek to fully understand the importance and implications of Nourseothricin today.

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Nourseothricin
n=1-4
Names
IUPAC name
pyridin-2-yl]amino]-5-amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
  • C1(2(C(=O)N1)N=C(N2)N3((((O3)CO)OC(=O)N)O)NC(=O)C(CCCN)N)O
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 , 100 kPa).

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

  1. ^ "Nourseothricin" (PDF).
  2. ^ Kochupurakkal BS, Iglehart JD (2013). "Nourseothricin N-acetyl transferase: a positive selection marker for mammalian cells". PLOS ONE. 8 (7) e68509. Bibcode:2013PLoSO...868509K. doi:10.1371/journal.pone.0068509. PMC 3701686. PMID 23861913.
  3. ^ Morgan, Christopher E.; Kang, Yoon-Suk; Green, Alex B.; Smith, Kenneth P.; Dowgiallo, Matthew G.; Miller, Brandon C.; Chiaraviglio, Lucius; Truelson, Katherine A.; Zulauf, Katelyn E.; Rodriguez, Shade; Kang, Anthony D.; Manetsch, Roman; Yu, Edward W.; Kirby, James E. (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". PLOS Biology. 21 (5) e3002091. doi:10.1371/journal.pbio.3002091. ISSN 1545-7885. PMC 10187937. PMID 37192172.
  4. ^ Krügel H, Fiedler G, Smith C, Baumberg S (1993). "Sequence and transcriptional analysis of the nourseothricin acetyltransferase-encoding gene nat1 from Streptomyces noursei". Gene. 127 (1): 127–31. doi:10.1016/0378-1119(93)90627-f. PMID 8486278.
  5. ^ Shen J, Guo W, Köhler JR (2005). "CaNAT1, a heterologous dominant selectable marker for transformation of Candida albicans and other pathogenic Candida species". Infection and Immunity. 73 (2): 1239–42. doi:10.1128/IAI.73.2.1239-1242.2005. PMC 547112. PMID 1566497. S2CID 37895453.
  6. ^ NTC properties, Jena Bioscience
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