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4696-76-8,MFCD28390297
Catalog No.:AA00I8IS

4696-76-8 | Bekanamycin

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1mg
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25mg
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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I8IS
Chemical Name:
Bekanamycin
CAS Number:
4696-76-8
Molecular Formula:
C18H37N5O10
Molecular Weight:
483.5139
MDL Number:
MFCD28390297
SMILES:
OC[C@H]1O[C@H](O[C@H]2[C@H](N)C[C@@H]([C@H]([C@@H]2O)O[C@H]2O[C@H](CN)[C@H]([C@@H]([C@H]2N)O)O)N)[C@@H]([C@H]([C@@H]1O)N)O
Properties
Computed Properties
 
Complexity:
639  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
15  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
15  
Hydrogen Bond Donor Count:
11  
Rotatable Bond Count:
6  
XLogP3:
-7.2  

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,1991,vol.34,p.1483-1492

[1]JournalofMedicinalChemistry,1991,vol.34,p.1468-1475

[1]MagneticResonanceinChemistry,1992,vol.30,p.841-846

[1]CarbohydrateResearch,1982,vol.109,p.271-275

[1]TetrahedronLetters,1980,vol.21,p.4981-4984

Literature

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Journal: PloS one 20130101

Title: Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20120715

Title: Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation.

Journal: Nature chemical biology 20111009

Title: Synthesis, antibacterial activities and molecular docking studies of Schiff bases derived from N-(2/4-benzaldehyde-amino) phenyl-N'-phenyl-thiourea.

Journal: Bioorganic & medicinal chemistry 20110915

Title: Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors.

Journal: Bioorganic & medicinal chemistry 20110801

Title: Influence of charge and structure on the coordination chemistry of copper aminoglycosides.

Journal: Dalton transactions (Cambridge, England : 2003) 20110227

Title: Construction of kanamycin B overproducing strain by genetic engineering of Streptomyces tenebrarius.

Journal: Applied microbiology and biotechnology 20110201

Title: Rational design and synthesis of potent aminoglycoside antibiotics against resistant bacterial strains.

Journal: Bioorganic & medicinal chemistry 20110101

Title: Antibacterial to antifungal conversion of neamine aminoglycosides through alkyl modification. Strategy for reviving old drugs into agrofungicides.

Journal: The Journal of antibiotics 20101101

Title: Role of aromatic rings in the molecular recognition of aminoglycoside antibiotics: implications for drug design.

Journal: Journal of the American Chemical Society 20100901

Title: Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20100801

Title: Thermodynamics and kinetics of association of antibiotics with the aminoglycoside acetyltransferase (3)-IIIb, a resistance-causing enzyme.

Journal: Biochemistry 20100518

Title: Design and synthesis of novel deoxybenzoin derivatives as FabH inhibitors and anti-inflammatory agents.

Journal: Bioorganic & medicinal chemistry letters 20100315

Title: Design, synthesis and biological evaluation of novel thiazole derivatives as potent FabH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: Synthesis, structure and structure-activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents.

Journal: European journal of medicinal chemistry 20091001

Title: Synthesis of C(7) modified chrysin derivatives designing to inhibit beta-ketoacyl-acyl carrier protein synthase III (FabH) as antibiotics.

Journal: Bioorganic & medicinal chemistry 20090901

Title: Synthesis, characterization and structure-activity relationship analysis of novel depsides as potential antibacterials.

Journal: European journal of medicinal chemistry 20090401

Title: Synthesis and biological evaluation of novel luteolin derivatives as antibacterial agents.

Journal: European journal of medicinal chemistry 20090201

Title: Cleavage of RNA oligonucleotides by aminoglycosides.

Journal: Organic & biomolecular chemistry 20090107

Title: Antiviral activity of geneticin against bovine viral diarrhoea virus.

Journal: Antiviral chemistry & chemotherapy 20080101

Title: Molecular determinants of antibiotic recognition and resistance by aminoglycoside phosphotransferase (3')-IIIa: a calorimetric and mutational analysis.

Journal: Journal of molecular biology 20070525

Title: Determination of tobramycin in human serum by capillary electrophoresis with contactless conductivity detection.

Journal: Electrophoresis 20060501

Title: Determination of tobramycin and impurities using high-performance anion exchange chromatography with integrated pulsed amperometric detection.

Journal: Journal of pharmaceutical and biomedical analysis 20060303

Title: Glycodiversification for the optimization of the kanamycin class aminoglycosides.

Journal: Journal of medicinal chemistry 20051006

Title: Thermodynamics of aminoglycoside binding to aminoglycoside-3'-phosphotransferase IIIa studied by isothermal titration calorimetry.

Journal: Biochemistry 20041123

Title: Identification and functional analysis of dTDP-glucose-4,6-dehydratase gene and its linked gene cluster in an aminoglycoside antibiotics producer of Streptomyces tenebrarius H6.

Journal: Current microbiology 20040801

Title: Regioselective glycosylation of neamine core: a facile entry to kanamycin B related analogues.

Journal: Organic letters 20040219

Title: Targeting RNA with small molecules.

Journal: Chembiochem : a European journal of chemical biology 20031006

Title: Antimycobacterial activity of phorbol esters from the fruits of Sapium indicum.

Journal: Journal of natural products 20030401

Title: Development and validation of capillary electrophoresis method for tobramycin with precapillary derivatization and UV detection.

Journal: Electrophoresis 20020601

Title: Aminoglycoside binding to human and bacterial A-Site rRNA decoding region constructs.

Journal: Bioorganic & medicinal chemistry 20011001

Title: In vitro selection of RNA against kanamycin B.

Journal: Molecules and cells 20010630

Title: Which aminoglycoside ring is most important for binding? A hydropathic analysis of gentamicin, paromomycin, and analogues.

Journal: Bioorganic & medicinal chemistry letters 20010122

Title: Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.

Journal: Cell 19930924

Title: In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.

Journal: Reviews of infectious diseases 19810101

Title: [Experimental study on renal tolerability of aminoglycosides butirosin and bekanamycin (author's transl)].

Journal: Arzneimittel-Forschung 19800101

Title: [Comparative studies on the problem of nephrotoxicity of the aminoglycosides: kanamycin, amikacin, butirosin and kanendomycin].

Journal: Verhandlungen der Deutschen Gesellschaft fur Innere Medizin 19760101

Title: Gao W, et al. Modulation of kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus viametabolic engineering. PLoS One. 2017 Jul 28;12(7):e0181971.

Title: Fosso MY, et al. Synthesis and Bioactivities of Kanamycin B-Derived Cationic Amphiphiles. J Med Chem. 2015 Dec 10;58(23):9124-32.

Title: Uchiyama T, et al. Presynaptic effects of bekanamycin at the frog neuromuscular junction. Reversibility by calcium and aminopyridines. Eur J Pharmacol. 1981 Jul 10;72(4):271-80.

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