Kanamycin B
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MedKoo CAT#: 540254

CAS#: 4696-76-8

Description: Kanamycin B is an inhibitor of protein translation and mammalian RNA splicing. It inhibits growth of gram negative bacteria, prevents formulation of the initiation complex, and decreases action potential amplitude in cardiac pacemaker cells.


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Kanamycin B purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540254
Name: Kanamycin B
CAS#: 4696-76-8
Chemical Formula: C18H37N5O10
Exact Mass: 483.254
Molecular Weight: 483.51
Elemental Analysis: C, 44.71; H, 7.71; N, 14.48; O, 33.09


Synonym: Bekanamycin; NK-1006; NK1006; NK 1006; Nebramycin V

IUPAC/Chemical 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)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol

InChi Key: SKKLOUVUUNMCJE-FQSMHNGLSA-N

InChi Code: 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

SMILES Code: NC[C@H]1O[C@@H]([C@@H]([C@H]([C@@H]1O)O)N)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)N)O)CO)N)N


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Zhang Y, He HM, Zhang J, Liu FJ, Li C, Wang BW, Qiao RZ. HPLC-ELSD determination of kanamycin B in the presence of kanamycin A in fermentation broth. Biomed Chromatogr. 2015 Mar;29(3):396-401. doi: 10.1002/bmc.3289. Epub 2014 Jul 17. PubMed PMID: 25042110.

2: Fosso MY, Shrestha SK, Green KD, Garneau-Tsodikova S. Synthesis and Bioactivities of Kanamycin B-Derived Cationic Amphiphiles. J Med Chem. 2015 Dec 10;58(23):9124-32. doi: 10.1021/acs.jmedchem.5b01375. Epub 2015 Dec 1. PubMed PMID: 26592740; PubMed Central PMCID: PMC5154386.

3: Truitt AR, Choi BE, Li J, Soto AM. Effect of Mutations on the Binding of Kanamycin-B to RNA Hairpins Derived from the Mycobacterium tuberculosis Ribosomal A-Site. Biochemistry. 2015 Dec 29;54(51):7425-37. doi: 10.1021/acs.biochem.5b00710. Epub 2015 Dec 17. PubMed PMID: 26560864.

4: Ni X, Li D, Yang L, Huang T, Li H, Xia H. Construction of kanamycin B overproducing strain by genetic engineering of Streptomyces tenebrarius. Appl Microbiol Biotechnol. 2011 Feb;89(3):723-31. doi: 10.1007/s00253-010-2908-5. Epub 2010 Oct 9. PubMed PMID: 20936279.

5: Fosso M, AlFindee MN, Zhang Q, Nziko Vde P, Kawasaki Y, Shrestha SK, Bearss J, Gregory R, Takemoto JY, Chang CW. Structure-activity relationships for antibacterial to antifungal conversion of kanamycin to amphiphilic analogues. J Org Chem. 2015 May 1;80(9):4398-411. doi: 10.1021/acs.joc.5b00248. Epub 2015 Apr 13. PubMed PMID: 25826012.

6: Yamasaki T, Narita Y, Hoshi H, Aburaki S, Kamei H, Naito T, Kawaguchi H. Synthesis and biological activity of 1-N-[4-(substituted)amidino and guanidino-2-hydroxybutyryl]kanamycins A and B. J Antibiot (Tokyo). 1991 Jun;44(6):646-58. PubMed PMID: 2071490.

7: Yung MW. Comparative ototoxicity of kanamycin A and kanamycin B in the guinea pig. Acta Otolaryngol. 1987 Jan-Feb;103(1-2):73-80. PubMed PMID: 3564930.

8: Carrier D, Chartrand N, Matar W. Comparison of the effects of amikacin and kanamycins A and B on dimyristoylphosphatidylglycerol bilayers. An infrared spectroscopic investigation. Biochem Pharmacol. 1997 Feb 7;53(3):401-8. PubMed PMID: 9065744.

9: Gao W, Wu Z, Sun J, Ni X, Xia H. Modulation of kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus via metabolic engineering. PLoS One. 2017 Jul 28;12(7):e0181971. doi: 10.1371/journal.pone.0181971. eCollection 2017. PubMed PMID: 28753625; PubMed Central PMCID: PMC5533434.

10: Mingeot-Leclercq MP, Van Schepdael A, Brasseur R, Busson R, Vanderhaeghe HJ, Claes PJ, Tulkens PM. New derivatives of kanamycin B obtained by modifications and substitutions in position 6''. 2. In vitro and computer-aided toxicological evaluation with respect to interactions with phosphatidylinositol. J Med Chem. 1991 Apr;34(4):1476-82. PubMed PMID: 2016725.

11: Song KM, Cho M, Jo H, Min K, Jeon SH, Kim T, Han MS, Ku JK, Ban C. Gold nanoparticle-based colorimetric detection of kanamycin using a DNA aptamer. Anal Biochem. 2011 Aug 15;415(2):175-81. doi: 10.1016/j.ab.2011.04.007. Epub 2011 Apr 15. PubMed PMID: 21530479.

12: Yung MW, Green C. Interaction of kanamycin A and kanamycin B with phospholipids. J Antibiot (Tokyo). 1987 Jun;40(6):862-7. PubMed PMID: 3610836.

13: Kato T, Yang G, Teo Y, Juskeviciene R, Perez-Fernandez D, Shinde HM, Salian S, Bernet B, Vasella A, Böttger EC, Crich D. Synthesis and Antiribosomal Activities of 4'-O-, 6'-O-, 4″-O-, 4',6'-O- and 4″,6″-O-Derivatives in the Kanamycin Series Indicate Differing Target Selectivity Patterns between the 4,5- and 4,6-Series of Disubstituted 2-Deoxystreptamine Aminoglycoside Antibiotics. ACS Infect Dis. 2015 Oct 9;1(10):479-86. doi: 10.1021/acsinfecdis.5b00069. Epub 2015 Aug 6. PubMed PMID: 27623314.

14: Portnoĭ IuA, Kartseva VD, Nikolaev GM, Chizhova NV. [Determination of the kanamycin B content of kanamycin preparations by column chromatography]. Antibiot Med Biotekhnol. 1987 Aug;32(8):583-5. Russian. PubMed PMID: 2823693.

15: Kumar V, Jones GS Jr, Blacksberg I, Remers WA, Misiek M, Pursiano TA. Aminoglycoside antibiotics. 3. Epimino derivatives of neamine, ribostamycin, and kanamycin B. J Med Chem. 1980 Jan;23(1):42-9. PubMed PMID: 6244410.

16: Van Schepdael A, Busson R, Vanderhaeghe HJ, Claes PJ, Verbist L, Mingeot-Leclercq MP, Brasseur R, Tulkens PM. New derivatives of kanamycin B obtained by combined modifications in positions 1 and 6". Synthesis, microbiological properties, and in vitro and computer-aided toxicological evaluation. J Med Chem. 1991 Apr;34(4):1483-92. PubMed PMID: 2016726.

17: Kwon M, Chun SM, Jeong S, Yu J. In vitro selection of RNA against kanamycin B. Mol Cells. 2001 Jun 30;11(3):303-11. PubMed PMID: 11459219.

18: Tebiakina AE, Shneerson AN, Braginskaia PS, Sinitsyna ZT, Korchagin VB, Korobitskaia AA. [Quantitative determination of the kanamycin B content in kanamycin preparations]. Antibiotiki. 1969 Aug;14(8):709-12. Russian. PubMed PMID: 4985086.

19: Dubost M, Pascal C, Terlain B, Thomas JP. [Detection of kanamycin B in kanamycin by thin layer chromatography]. J Chromatogr. 1973 Nov 7;86(1):274-8. French. PubMed PMID: 4765317.

20: Toda S, Nakagawa S, Naito T. Aminoglycoside antibiotics. X. chemical conversion of kanamycin B to kanamycin C and 6'-deoxy-kanamycin C. J Antibiot (Tokyo). 1977 Nov;30(11):1002-3. PubMed PMID: 591453.