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CAS No. : | 4696-76-8 | MDL No. : | MFCD01683541 |
Formula : | C18H37N5O10 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SKKLOUVUUNMCJE-FQSMHNGLSA-N |
M.W : | 483.51 | Pubchem ID : | 439318 |
Synonyms : |
Kanamycin B;Kanendomycin;NK-1006;Nebramycin V
|
Num. heavy atoms : | 33 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 15.0 |
Num. H-bond donors : | 11.0 |
Molar Refractivity : | 107.15 |
TPSA : | 288.4 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -14.36 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | -7.2 |
Log Po/w (WLOGP) : | -7.32 |
Log Po/w (MLOGP) : | -5.83 |
Log Po/w (SILICOS-IT) : | -7.46 |
Consensus Log Po/w : | -5.38 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 4.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | 2.09 |
Solubility : | 60100.0 mg/ml ; 124.0 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.86 |
Solubility : | 35300.0 mg/ml ; 73.1 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 4.77 |
Solubility : | 28200000.0 mg/ml ; 58300.0 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 6.5 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
b. Physico-chemical properties of 3'-chloro-3'-deoxykanamycin B: Rf value of thin layer chromatography: Plate: silica gel glass plate (manufactured by Merck & Co.) Developing solvent: upper layer [of chloroform-methanol-water-aqueous ammonia (2.0:1.5:0.5:1.0)]-methanol (1:1) 3'-chloro-3'-deoxykanamycin B: 0.55 Kanamycin B: 0.39 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.66 g | To a solution of kanamycin B (2.00 g, 4.14 mmol) in water (6 mL) was added CuSO4 (33 mg, 0.21 mmol) and the resulting mixture was stirred for 15 min, then triethylamine (4.18 g, 41.4 mmol) was added in one portion. After the mixture was stirred for 20 min at ice-bath temperature, triflyl azide solution in acetonitrile (21 mL, 1.5 N, 31.5 mmol) was added dropwise in a period of 15 min. After 2 h, the ice-bath was removed and the mixture was stirred for another 10 h at room temperature. Then the solvent was removed and the crude product was treated with the mixture of acetic anhydride (6 mL) and pyridine (9 mL). After stirring overnight, the reaction mixture was poured into 150 mL of brine, and the resulting precipitates were collected by filtration. The crude product was purified by column chromatography on silica gel, using petroleum ether/ethyl acetate (6:1 to 3:1) as eluent. The resulting product was dissolved in 60 mL of methanol, and catalytic amount of sodium methoxide was added. When TLC assay showed that the reaction was completed, the reaction mixture was neutralized with cation-exchange resin and the solvent was removed. The yielded product (1.66 g, 2.71 mmol) was dissolved in 30 mL of pyridine, tert-butyldiphenylchlorosilane (1.50 g, 5.5 mmol) and catalytic amount of DMAP were added to the solution. After stirring for 48 h at room temperature, the solvent was removed and the crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1) as eluent. Finally, 2.08 g (2.44 mmol, 59% overall yield) of title product was obtained as a colorless semisolid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With DeltagenS2 mutant of GenS2 aminotransferase; L-glutamate; In aq. buffer;pH 7.5;Enzymatic reaction; | General procedure: Gentamicin A2 (3) purified from the DeltagenS2DeltagenK mutant of M. echinospora ATCC15835 (see Supplemental Experimental Procedures, Method S1, forthe protocol of purification) was used as a substrate in assays testing the activity of GenD2 as a 300-dehydrogenase, GenS2 as a 3''-transaminase, andGenN as a 3''-N-methyltransferase. A typical reaction (100 ml) contained substrate (400 mM), NAD+ or NADP+ (2.5 mM), L-glutamate (1 mM, when GenS2was present), SAM (2 mM, when GenN was present), and purified enzyme(s) (30 mM each) in Tris-HCl buffer (50 mM, pH 7.5). To test the deamination activity of GenS2 and the subsequent ketoreductase activity of GenD2 (the reverse reactions), kanamycin B (11) and tobramycin (12) were used as substrates. A typical reaction mixture consisted of substrate (400 mM), NADH or NADPH(2.5 mM), 2-oxoglutarate (1 mM, when GenS2 was present), and purified enzyme(s) (30 mM) in Tris-HCl buffer (50 mM, pH 7.5). Kanamycin and tobramycin were used as substrate analogs to test the putative 3''-N-methyltransferase activity of GenN. A typical reaction mixture contained substrate (400 mM),SAM (2 mM), and purified GenN (30 mM) in Tris-HCl buffer (50 mM, pH 7.5).Reaction mixtures were incubated at 30 C and quenched by addition of chloroform (100 ml) followed by vigorous vortexing. Precipitated protein was removed by centrifugation. Ten to twenty microliters of the aqueous supernatant were analyzed by either LC-ESI-MS or LC-ESI-HRMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium carbonate; In water; isopropyl alcohol; at 30.0℃; for 6h; | Weighkanamycin B 9.66g (20mmol), anhydrous sodium carbonate 10.6g (100mmol), whichwas dissolved in 50mL of water, 50mL of isopropanol was added, and then weigheddi-tert-butyl dicarbonate 26.2g (120mmol) was added thereto, at 30 C for 6 Hours,filtered, and the filtrate was collected to give 1,3,2',6',3''-penta-N-tert-butoxycarbonylkanamycin B 18.5g, yield 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.3% | With sodium carbonate In ethanol; dichloromethane; water at 25℃; for 16h; | 1-6; 1-2 Add 50g of kanamycin B, 50g of sodium carbonate, 200g of water, 200g of ethanol and 400g of dichloromethane into the reaction kettle, stir evenly; add 120g of p-toluenesulfonate at 030 (25 in this example) The acid chloride is stirred and reacted at 25° C. for 16 hours under three solvent systems of water-ethanol-dichloromethane, and the reaction of the central control raw material is complete.400g of hexane was added, stirred for 2 hours and then dried by suction filtration to obtain 120g of intermediate with a yield of 92.3% and a purity of 95.90% by HPLC (see Figure 1). |