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11011-72-6

11011-72-6 Structure

11011-72-6 Structure
IdentificationBack Directory
[Name]

Bluensomycin
[CAS]

11011-72-6
[Synonyms]

U-12898
U-12898D
Bluensin
Aids010599
Aids-010599
Bluensomycin
Nsc111930 (sulfate salt)
2-O-[5-Deoxy-3-C-(hydroxymethyl)-2-O-[2-deoxy-2-(methylamino)-α-L-glucopyranosyl]-α-L-lyxofuranosyl]-1-(amidinoamino)-1-deoxy-5-O-carbamoyl-D-scyllo-inositol
2-O-[2-O-[2-(Methylamino)-2-deoxy-α-L-glucopyranosyl]-3-C-hydroxymethyl-5-deoxy-α-L-lyxofuranosyl]-1-(aminoiminomethylamino)-5-O-carbamoyl-1-deoxy-D-scyllo-inositol
D-myo-Inositol, O-2-deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-(hydroxymethyl)-α-L-lyxofuranosyl-(1→2)-1-[(aminoiminomethyl)amino]-1-deoxy-, 5-carbamate
D-Scyllo-inositol, o-2-deoxy-2-(methylamino)-.alpha.-L-glucopyranosyl-(1.fwdarw.2)-o-5-deoxy-3-C-(hydroxymethyl)-.alpha.-L-lyxofuranosyl-(1.fwdarw.2)-1-[(aminoiminomethyl)amino]-1-deoxy-, 5-carbamate
[Molecular Formula]

C21H39N5O14
[MDL Number]

MFCD00864961
[MOL File]

11011-72-6.mol
[Molecular Weight]

585.56
Hazard InformationBack Directory
[Originator]

Bluencomycin,Shanghai Lansheng Corporation
[Definition]

ChEBI: Bluensomycin is an amino sugar.
[Manufacturing Process]

Bluensomycin was obtained from cultures of Streptomyces verticillus, or the same substance produced by any other means. For example antibiotic was prepared by growing of Streptomyces bluensis NRRL 2876 biological way and isolation from cultural solution by adsorption with a cation-exchange resin or a capillary adsorption method by elution with water-acid solution at pH from 1 to 6 or acidic water solution of acetone. 5350 L of cultivating liquid with pH 8.2 was mixed with 16 kg oxalic acid acidified with 1 N sulfuric acid to pH 2.9 and was filtered through about 160 kg fossil flour and washed with 500 L water. The filtrate (about 5400 L) was alkalified to pH 7.8-8 with 10% sodium hydroxide and was filtered through fossil flour filter. Then it was passed through two column with polyacrylic acid cation exchange resin in sodium form (US Patent No. 2,915,432). Each column was 35 cm in diameter and contained 0.126 kg of above resin.
The filtrate (5300 L) was passed with rate 19 L/minute. Then the columns were washed with deionized water, 1 N sulfuric acid to pH 1.2-1.5, and at last eluted with 4x100 L water. About 200 L of column effluent was alkalifed to pH 6.4 with 10% sodium hydroxide. The 1-st column effluent was mixed with 1200 g of activated carbon, the second effluent was mixed with 850 g of coal (1 g coal per 1 g dissolved product). The mixture was thoroughly stirred and filtered. Each coal precipitate was washed 3x10 L with water and 200 L 15% water acetone.
Water acetone effluent from the 1-st column (187 L) was dried and gave 1034 g of bluensomycin, the second gave 777 g. The portions of antibiotic were combined and purified by chromatography. The column (high 1.2 m, volume 155 L, with sea sand, adsorbent cotton and fossil flour as the carrier) was used. It was washed with 150 L of deionized water and 300 L 10% water acetone (rate 410 ml per minute). A fraction 101-127 L water acetone gave 640 g bluensomycin after drying. The IR and UV spectra, element analysis confirmed the structure of prepared product and its purity.
[Therapeutic Function]

Antibiotic
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