Streptomycin oxidation

Drugs can also Interfere with laboratory results by negating certain nonspecific oxidation and reduction reactions essential for the chemical assay. Penicillin, streptomycin and ascorbic acid are known to react with cupric Ion thus, false positive results for glucose may occur If a copper reduction method Is used. If the specific enzymatic glucose-oxidase method Is employed, ascorbic acid can cause a false negative result by preventing the oxidation of a specific chromogen In the reaction. 

Several compounds of this type, formally derived from aldoses by oxidation of the terminal CH2OH group to -CHO, have been prepared. Dialdoses arise as intermediates in structural studies, but they are also valuable starting materials for synthetic conversions, in particular for natural-product synthesis. A branched-chain dialdose, streptose (167), occurs as a component of the antibiotic streptomycin. The structure of streptose was elucidated after extensive investigations of its derivatives and transformation products.371 The 2,5-dimethoxytetrahydrofuran fulvanol (168), an analogue of apiose, has been isolated from the plant Hemerocallis fulva 12... 

Streptomycin was inactivated by reducing and oxidizing agents. The bacteriostatic-activity of this antibiotic for Escherichia coli was reduced in the presence of cysteine, sodium thioglycolate, stannous chloride, sodium bisulfite, sodium hydrosulfide, sodium formate and sodium thiosulfate. Cysteine was the most active. Denkelwater, Cook and Tishler found that the cysteine inactivation of streptomycin could be reversed by iodine presumably cystine was formed during this process. Rake and Donovick inactivated streptomycin with semi-carbazide hydrochloride in order to test the sterility of concentrated streptomycin solutions. The inactivation of streptomycin by compounds containing sulfhydryl groups has been discussed by Cavallito. ... 

Hydrogenation of the crystalline streptomycin trihydrochloride-calcium chloride double salt in aqueous solution with platinum oxide catalyst at atmospheric pressure or with Raney nickel catalyst at 100-140 atmospheres and 150° also yielded dihydrostreptomycin. Acid hydrolysis of dihydrostreptomycin gave streptidine and N-methyl-L-glucosamine. Hence, the reduction involved the nitrogen-free moiety, streptose. 

Fried and Wintersteiner - oxidized streptomycin trihydrochloride with bromine water to an amorphous, antibiotically inactive product The relatively strongly acidic nature of this substance, which they named streptomycinic acid, was demonstrated by electrometric titration. In the infrared spectral region the substance exhibited an absorption maximum at a wave length of 6.06m, which was partially displaced to 5.81m when the spectrum was observed in the presence of deuterium oxide and deuterium chloride. A shift of this type is usually found with dipolar ions and was taken therefore as an indication of the expected dipolar ion character of streptomycinic acid. 

A number of points regarding the chemical behavior of the streptose moiety are anomalous and will bear comment. Although a free carbonyl group seems established, streptomycin itself shows no carbonyl absorption in the ultraviolet region. Derivatives of the acyclic or aldehydo structure have hitherto exhibited such absorption. Oxidation of this aldehyde substituent to the carboxyl stage or its reduction to either the carbinol or hydrocarbon did not affect the resistance of the tertiary hydroxyl toward acetylation. However, conversion of both aldehyde functions in streptose to the carboxyl stage of oxidation made the tertiary hydroxyl easily esterifiable. ... 

Streptose (the formylpentose present in the antibiotic, streptomycin) and 5-hydroxystreptose (in the related hydroxystreptomycin) were for a long time the only natural dicarbonyl compounds known. Recently, however, some dicarbonyl compounds have been isolated from the products of the microbial oxidation of sugars, and a hexos-5-ulose has been found in an antibiotic. 

In vitro quantitative antibacterial activity was evaluated using Alamar Blue Assay [56]. It is a colorimetric oxidation-reduction assay which involves the addition of Alamar blue dye as an indicator. It evaluates the metabolic activity of the microorganisms. The activity of the evaluated drug is expressed as minimum inhibitory concentration ( 0,g/ml). Sampangine, SAMM2 and SAM MMl were tested for their activity against Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa ATCC 15442, Bacillus subtilus ATCC 6633, and E. coli ATCC 10536. Streptomycin was used as a positive control. 

The most difficult total syntheses in this class of pseudotrisaccharides were those of streptomycin and dihydrostreptomycin. About 35 years after their discovery and the elucidation of their structure, S. Umezawa and colleaguessucceeded in synthesising these compounds. The glycosyl derivative (I), prepared through several steps from streptobiosaminide, was condensed with the protected streptidine (II), to yield dihydrostreptomycin, after deprotection. Subsequent oxidation with DMSO/dicyclo-hexylcarbodiimide (DCC) produced streptomycin... 

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