Nourseothricin sulfate

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Nourseothricin sulfate
Category Antibiotics
Catalog number BBF-04117
CAS 96736-11-7
Molecular Weight 600.60
Molecular Formula C19H36N8O12S

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Description

An antibiotic in the streptothricin class of antibiotics.

Specification

Synonyms streptothricin
IUPAC Name [(2R,3R,4S,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;sulfuric acid
Canonical SMILES C1C(C2C(C(=O)N1)N=C(N2)NC3C(C(C(C(O3)CO)OC(=O)N)O)NC(=O)CC(CCCN)N)O.OS(=O)(=O)O
InChI InChI=1S/C19H34N8O8.H2O4S/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;1-5(2,3)4/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);(H2,1,2,3,4)/t7-,8+,9+,11+,12-,13+,14-,15-,17+;/m0./s1
InChI Key UDVWKDBCMFLRQW-TWRCRAKCSA-N

Properties

Boiling Point 348.5°C at 760 mmHg
Density 0.987 g/cm3

Reference Reading

1. Molecular structure and evolution of the conjugative multiresistance plasmid pRE25 of Enterococcus faecalis isolated from a raw-fermented sausage
Franziska Schwarz, Vincent Perreten, Michael Teuber Int J Food Microbiol . 2003 Dec 1;88(2-3):325-9. doi: 10.1016/s0168-1605(03)00195-8.
Plasmid pRE25 from Enterococcus faecalis transfers resistances against kanamycin, neomycin, streptomycin, clindamycin, lincomycin, azithromycin, clarithromycin, erythromycin, roxithromycin, tylosin, chloramphenicol, and nourseothricin sulfate by conjugation in vitro to E. faecalis JH2-2, Lactococcus lactis Bu2, and Listeria innocua L19. Its nucleotide sequence of 50237 base pairs represents the largest, fully sequenced conjugative multiresistance plasmid of enterococci (Plasmid 46 (2001) 170). The gene for chloramphenicol resistance (cat) was identified as an acetyltransferase identical to the one of plasmid pIP501 of Streptococcus agalactiae. Erythromycin resistance is due to a 23S ribosomal RNA methyl transferase, again as found in pIP501 (ermB). The aminoglycoside resistance genes are packed in tandem as in transposon Tn5405 of Staphylococcus aureus: an aminoglycoside 6-adenyltransferase, a streptothricin acetyl transferase, and an aminoglycoside phosphotransferase.). Identical resistance genes are known from pathogens like Streptococcus pyogenes, S. agalactiae, S. aureus, Campylobacter coli, Clostridium perfringens, and Clostridium difficile. pRE25 is composed of a 30.5-kbp segment almost identical to pIP501. Of the 15 genes involved in conjugative transfer, 10 codes for putative transmembrane proteins (e.g. trsB, traC, trsF, trsJ, and trsL). The enterococcal part is joined into the pIP501 part by insertion elements IS1216V of E. faecium Tn1545 (three copies), and homologs of IS1062 (E. faecalis) and IS1485 (E. faecium). pRE25 demonstrates that enterococci from fermented food do participate in the molecular communication between Gram-positive and Gram-negative bacteria of the human and animal microflora.

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