Butirosin

Butirosin Chemische Eigenschaften,Einsatz,Produktion Methoden

• Originator

  Butirosin,SigmaAldrich

• Verwenden

  Antibacterial.

• Manufacturing Process

  Ambutyrosin is the another name of butirosin. Ambutyrosin obtained from fermentation broths of Bacillus circulans contains a major proportion of N1-(4- amino-2-hydroxybutyryl)-4-O-2,6-diamino-2,6-didexy-D-glucopyranosyl)-5-O-D-xelofuranosyl-2-deoxystreptamine (ambutyrosin A) and a minor proportion (up to 10-15%) of N1-(4-amino-2-hydroxybutyryl)-4-O-2,6-diamino-2,6- didexy-D-glucopyranosyl)-5-O-D-ribofuranosyl-2-deoxystreptamine (ambutyrosine B). A process for preparation of ambutyrosin by semisynthetic procedure of acylating of 5-β-D-xylofuranosylneamine or 5-β- ribofuranosylneamine is described below.
  Preparation of 5-β-D-pentofuranosyIneamine: ambutyrosin A (1.0 g) in 30 ml of 0.5 N sodium hydroxide solution was refluxed for one hour, then neutralized with 6 N hydrochloric acid and applied on a column of Amberlite CG-50 (NH4+ form, 30 ml). The column was washed with water (ca. 100 ml) until the ninhydrin test became negative, and then eluted with 0.2 N ammonium hydroxide. Biologically active fractions were collected, concentrated in vacuum to 5 ml and treated with 5 ml of methanol to induce precipitation. It was further purified by re-precipitation from aqueous methanol to yield 607 mg (65%) of deacylated ambutyrosin A hereafter referred to as DA1.
  The wash water of the above CG-50 column was adjusted to pH 7.0 and applied on a column of Amberlite IR-120 (H+ form, 30 ml). The column was washed with water and then eluted with 1 N ammonium hydroxide. Ninhydrin-positive fractions were combined, treated with active carbon and neutralized with IRC-50 resin (H+ form). The solution was concentrated to a small volume, treated with ethanol, and kept in the cold overnight to yield 160 mg (75%) of γ-amino-α-hydroxybutyric acid as colorless needles which melted at 217°C-218°C. [α]D23= -30.3° (c=1.0%, H2O).
  The above experiments were also carried out on 1.0 g of ambutyrosin B yielding 579 mg (62%) of deacylated ambutyrosin B, hereafter called DA2.
  L-(-)-γ-benzyloxycarbonylamino-α-ydroxybutyric acid: L-(-)-γ-amino-α- hydroxybutyric acid (7.4 g, 0.062 mole) was added to 50 ml of aqueous sodium 3 hydroxide solution (5.2 g, 0.13 mole). To the solution was added dropwise 11.7 g (0.068 mole) of carbobenzoxy chloride with stirring at 0°C to 5°C for one hour. The reaction mixture was washed with 50 ml of ether, adjusted to pH 2 with dilute hydrochloric acid, and extracted with four 80-ml portions of ether. The extracts were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuum, and the residue was crystallized from benzene to give 11.6 g (74%) of 4 colorless plates. M.P: 78.5°-79.5°C.
  N-Hydroxysuccinimide ester of L-(-)-γ-benzyloxycarbonylamino-α-hydroxybutyric acid: a solution of L-(-)-γ-benzyloxycarbonylamino-α- hydroxybutyric acid (10.6 s g, 0.042 mole) and N-hydroxysuccinimide (4.8 g, 0.042 mole) in 200 ml of ethyl acetate was cooled to 0°C and added to 8.6 g (0.042 mole) of dicyclohexylearbodiimide. The mixture was stirred overnight at 5°C. The dicyclohexylurea which separated was removed by filtration, and the filtrate was concentrated in vacuum. The product was obtained as colorless plates. Yield: 13.4 g (92%). M.P: 117°-118°C [α]D23= +1.5° (c= 2.0%, CHCl3).
  N-(Benzyloxycarbonyloxy)succinimide: N-hydroxysuccinimide (23 g, 0.2 mole) was dissolved in 200 ml of aqueous NaOH solution (9 g, 0.22 mole). To the stirred solution was added dropwise 34 g (0.2 mole) of carbobenzoxy chloride with water-cooling. The mixture was stirred overnight at room temperature, and the precipitate which separated was collected by filtration, washed with water, and air dried. Yield: 41.1 g (82%). Recrystallization from benzene-n-hexane (10:1) gave colorless prisms melting at 78°-79°C.
  6'-Carbobenzoxy-DA1 and 1,6'-dicarbobenzoxy-DA1:
  To a solution of 9.1 g (20 mmoles) of above prepared DA1 in 150 ml of water and 60 ml of tetrahydrofuran (THF)

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