Kanamycin B
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| Category | Antibiotics |
| Catalog number | BBF-01885 |
| CAS | 4696-76-8 |
| Molecular Weight | 483.51 |
| Molecular Formula | C18H37N5O10 |
| Purity | ≥95% |
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Description
Kanamycin B is an aminoglycoside antibiotic produced by the strain of Str. kanamyceticus. It is used to treat the infection of gram-positive bacteria, gram-negative bacteria and mycobacterium tuberculosis.
Specification
| Related CAS | 29701-07-3 (sulfate) |
| Synonyms | Bekanamycin; NK-1006; NK1006; NK 1006; Nebramycin V; Aminodeoxykanamycin; (1R,2S,3S,4R,6S)-4,6-diamino-3-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-2-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | -20 °C |
| IUPAC Name | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4-diol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)N)N |
| InChI | InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1 |
| InChI Key | SKKLOUVUUNMCJE-FQSMHNGLSA-N |
Properties
| Appearance | White Acicular Crystalline |
| Application | aminoglycoside antibiotic. |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Boiling Point | 807.7°C at 760 mmHg |
| Melting Point | >175°C (dec.) |
| Density | 1.59 g/cm3 |
| Solubility | Soluble in Aqueous Acid (Slightly), DMSO, Methanol (Slightly, Heated, Sonicated), Water (Sparingly) |
Reference Reading
1.HPLC-ELSD determination of kanamycin B in the presence of kanamycin A in fermentation broth.
Zhang Y1, He HM, Zhang J, Liu FJ, Li C, Wang BW, Qiao RZ. Biomed Chromatogr. 2015 Mar;29(3):396-401. doi: 10.1002/bmc.3289. Epub 2014 Jul 17.
A novel method for the direct determination of kanamycin B in the presence of kanamycin A in fermentation broth using high performance liquid chromatography with evaporative light scattering detector (HPLC-ELSD) was developed. An Agilent Technologies C18 column was utilized, evaporation temperature of 40°C and nitrogen pressure of 3.5 bar, the optimized mobile phase was water-acetonitrile (65:35, v/v), containing 11.6 mm heptafluorobutyric acid (isocratic elution with flow rate of 0.5 mL/min) with the gain 11. Kanamycin B was eluted at 5.6 min with an asymmetry factor of 1.827. The method showed good linearity over the concentration range of 0.05 to 0.80 mg/mL for the kanamycin B (r(2) = 0.9987). The intra-day and inter-day coefficients of variation obtained from kanamycin B were less than 4.3%. Mean recovery of kanamycin B from spiked fermentation broth was 95%. The developed method was applied to the determination of kanamycin B without any interference from other constituents in the fermentation broth.
2.Effect of Mutations on the Binding of Kanamycin-B to RNA Hairpins Derived from the Mycobacterium tuberculosis Ribosomal A-Site.
Truitt AR1, Choi BE1, Li J1, Soto AM1. Biochemistry. 2015 Dec 29;54(51):7425-37. doi: 10.1021/acs.biochem.5b00710. Epub 2015 Dec 17.
Kanamycin is an aminoglycoside antibiotic used in the treatment of drug-resistant tuberculosis. Mutations at the rRNA A-site have been associated with kanamycin resistance in Mycobacterium tuberculosis clinical isolates. Understanding the effect of these mutations on the conformation of the M. tuberculosis A-site is critical for understanding the mechanisms of antibiotic resistance in M. tuberculosis. In this work, we have studied RNA hairpins derived from the M. tuberculosis A-site, the wild type and three mutants at the following positions (M. tuberculosis/Escherichia coli numbering): A1400/1408 → G, C1401/1409 → U, and the double mutant G1483/1491 C1401/1409 → UA. Specifically, we used circular dichroism, ultraviolet spectroscopy, and fluorescence spectroscopy to characterize the conformation, stability, and binding affinity of kanamycin-B and other aminoglycoside antibiotics for these RNA hairpins. Our results show that the mutations affect the conformation of the decoding site, with the mutations at position 1401/1409 resulting in significant destabilizations.
3.Synthesis and Bioactivities of Kanamycin B-Derived Cationic Amphiphiles.
Fosso MY1, Shrestha SK1, Green KD1, Garneau-Tsodikova S1. J Med Chem. 2015 Dec 10;58(23):9124-32. doi: 10.1021/acs.jmedchem.5b01375. Epub 2015 Dec 1.
Cationic amphiphiles derived from aminoglycosides (AGs) have been shown to exhibit enhanced antimicrobial activity. Through the attachment of hydrophobic residues such as linear alkyl chains on the AG backbone, interesting antibacterial and antifungal agents with a novel mechanism of action have been developed. Herein, we report the design and synthesis of seven kanamycin B (KANB) derivatives. Their antibacterial and antifungal activities, along with resistance/enzymatic, hemolytic, and cytotoxicity assays were also studied. Two of these compounds, with a C12 and C14 aliphatic chain attached at the 6″-position of KANB through a thioether linkage, exhibited good antibacterial and antifungal activity, were poorer substrates than KANB for several AG-modifying enzymes, and could delay the development of resistance in bacteria and fungi. Also, they were both relatively less hemolytic than the known membrane targeting antibiotic gramicidin and the known antifungal agent amphotericin B and were not toxic at their antifungal MIC values.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
