Streptomycin chemical structure

The widespread interest in fundamental information regarding the molecular structure of such an important antibiotic facilitated the rapid elaboration of the structure of streptomycin. The substance has been well characterized with regard to its antibacterial activity, protective and toxic effects and other biological properties. The investigations which led to the elucidation of the chemical structure of streptomycin form a noteworthy display of the more modern methods for structural determination and comprise a valuable contribution to carbohydrate chemistry. 

The aminoglycoside antibiotics include streptomycin, neomycin, gentamicin, amikacin, tobramycin and kanamycin. They have a chemical structure of amino sugars joined by a glycoside... 

Chemical Structure Aminoglycosides are antimicrobial agents with dissimilar structures it is impossible to represent aminoglycosides with a single general structure. The following is the structure of streptomycin ... 

The antibiotic cycloheximide was isolated in 1946 from actinomycetes fungi producing streptomycin (Leach et al., 1947 Whiffen, 1948), and later was also produced from Streptomyces noursei fungi (Brown and Hazen, 1956). Naramycin A, isolated in Japan from Streptomyces naranensis fungi, is also cycloheximide (Okuda, 1959). Cycloheximide was first used in agriculture in 1948 under the name Actidione in the USA. Its chemical structure is 4 (2/ )-2-[(15,35,5S)-(3,5-dimethyl-... 

Fig. 3. Aminoglycoside antibiotics chemical structures of streptomycin (/) and dihydrostreptomycin (//). Ring = streptidine ring 5=streptose ring C=iV-methyl-L-glucosa-mine ring D = streptobiosamine...

Streptomycin and dihydrostreptomycin have very similar chemical structures and so many of the chemical methods which are available are equally applicable to both antibiotics. Certain procedures have a measure of specificity however and may be used for the determination of one of the substances in the presence of the other. The B.P. relies upon microbiological assay (see p. 813) for determination of the potency of both these antibiotics, which are official in the form of their sulphates. 

The elucidation of chemical structure of streptomycin, an antibiotic produced by Streptomyces griseus, and other streptomyces species has now been virtually completed. 

Although the aminoglycosides such as streptomycin, neomycin and the gen-tamicins have a long and storied history as treatments for antibacterial infections, particularly in the early days when streptomycin was a treatment for both infected wounds and also for tuberculosis, few modifications of the basic molecule(s) went into clinical use, mainly due to the complexity of chemical modification of saccharidic-based structures. Thus, we do not discuss this class further or molecules such as the rifamycins and their manifold derivatives. Instead, due to space constraints, we show how p-lactams,... 

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. ... 

Hygromycin A [1] is classified chemically as a member of the aminocyclitols antibiotic family represented by streptomycin and kanamycin. Its structure determined by degradation and spectral analyses, (72, 13) revealed that it consists of three unusual moieties, namely S-dehydro-a-L-fucofuranose, ( )-3-(3,4-dihydroxyphenyl)-2-methylacrylic acid, and an aminocyclitol (2L-2-amino-2-deoxy-4,5-0-methylene- eo-inositol). The 5-dehydro-a-L-fucofuranose moiety is attached by a glycosidic linkage of the 4-hydroxy position of ( )-3-... 

To address this organ-directed idiosyncratic toxicity we will highlight two drugs, cisplatin and streptomycin, which are chemically distinct (see structure in Figure 13.8) yet have an intriguing similarity of spectrum of activities. 

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