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66-86-4-Neomycin C Neomycin C

Neomycin C

For research use only. Not for therapeutic Use.

  • CAT Number: M019908
  • CAS Number: 66-86-4
  • Molecular Formula: C23H46N6O13
  • Molecular Weight: 614.65
  • Purity: ≥95%
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Related Small Molecules: VANADIUM(V) OXYTRIETHOXIDE     G-protein coupled receptor OR3     1-Naphthalenesulfonylchloride,5-amino-(9CI)    

Neomycin C (Cat.No:M019908) is a stereoisomer of neomycin B, the active component in neomycin. Despite its similarity to neomycin B, neomycin C is thought to only have approximately 35% of the biological activity of neomycin B. Neomycin C sulfate is a highly purified component found in standard grade neomycin. Aminoglycosides target the 30S ribosomal subunit resulting in an inability to read mRNA ultimately producing a faulty or nonexistent protein.


Catalog Number M019908
CAS Number 66-86-4
Synonyms

5-amino-2-(aminomethyl)-6-[5-[3,5-diamino-2-[3-amino-6-(aminomethyl)-4 ,5-dihydroxy-oxan-2-yl]oxy-6-hydroxy-cyclohexyl]oxy-4-hydroxy-2-(hydro xymethyl)oxolan-3-yl]oxy-oxane-3,4-diol;neomycin C;4-O-(2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl)-5-O-[3-O

Molecular Formula C23H46N6O13
Purity ≥95%
Target Antibiotic
Storage Desiccate at -20°C
IUPAC Name (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
InChI InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
InChIKey PGBHMTALBVVCIT-VZXHOKRSSA-N
SMILES C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N
Reference

1.Kudo F, Kawashima T, Yokoyama K, Eguchi T. Enzymatic preparation of neomycin C from ribostamycin. J Antibiot (Tokyo). 2009 Nov;62(11):643-6. doi: 10.1038/ja.2009.88. Epub 2009 Aug 28. PubMed PMID: 19713992.<br />
2.Driver JL, Thiex N, Raynie D, Ofitserova M, Pickering M. Single-laboratory validation for the quantification of neomycin B and neomycin C in animal feeds by liquid chromatography fluorescence detection with post-column derivatization. J AOAC Int. 2009 Jan-Feb;92(1):34-41. PubMed PMID: 19382560.<br />
3.Umezawa S, Nishimura Y. Total synthesis of neomycin C. J Antibiot (Tokyo). 1977 Feb;30(2):189-91. PubMed PMID: 849920.<br />
4.Robertson JH, Baas R, Yeager RL, Tsuji K. Antimicrobial activity of neomycin C against Staphylococcus epidermidis. Appl Microbiol. 1971 Dec;22(6):1164-5. PubMed PMID: 5137586; PubMed Central PMCID: PMC376505.<br />
5.KOOIJ R. Allergic contact dermatitis due to neomycin. Cross-sensitivity with other antibiotics; and positive patch tests with the isomeric compounds neomycin B and neomycin C and with neamine. S Afr Med J. 1961 May 20;35:406-11. PubMed PMID: 13753040.<br />
6.CARPENTER OS, SOKOLSKI WT. A biologic assay for neomycin B in the presence of neamine and neomycin C. Antibiot Annu. 1955-1956;3:383-90. PubMed PMID: 13355298.

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