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Molecule of the Month

Chemistry and chemical biology of tetracyclines
Rafal Klajn
Institute of Organic Chemistry, PAN
Warsaw, Poland

It was in 1948 when Benjamin M. Duggar, Professor of Plant Physiology at the University of Wisconsin and a consultant to Lederle, first isolated tetracycline in quite particular circumstances. Dr. Duggar extracted aureomycin from a type of soil found particularly in the vicinity of cemeteries. This special soil contained a unique fungi which had the annihilating effect upon disease bacteria.

The era of tetracyclines had dawned!

The substance isolated by Duggar (7-chlorotetracycline) [1] was named aureomycin1 after its yellowish color. Aureomycin differed much from the others antibiotics known till then, mainly because of its broad spectrum of antimicrobial properties and a relatively low toxicity. Terramycin (5-hydroxytetracycline)2 was isolated two years later [2] by fermentation of the actinomycete, Streptomyces rimosus (Finley et al.). Production of the parent tetracycline itself by catalytic hydrogenolysis of aureomycin [3] was reported in 1953, subsequently, this compound was prepared by cultivation of certain strains of Streptomyces albo-niger [4].

Since then, a remarkable number of investigations has been recorded in order to define and rationalize the biogenetic origin and of the chemical, microbiological, pharmacological, and clinical properties of tetracyclines. Simultaneously, a search of new members of the series has been pressed on a world-wide scale [5]. As a result, a number of new tetracyclines has joined chlorotetracycline, oxytetracycline and tetracycline in widespread application in medical practice.

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