Antibiotics and process for producing the same using streptomyces caelestis

1,125,723. Desdanine and related antibiotics. UPJOHN CO. 8 Oct., 1965 [27 Nov., 1964], No. 42820/65. Heading C2A. [Also in Division A5] An antibiotic desdanine is coproduced with the known antibiotic celesticetin and a further antibiotic desdamethine, ethesdanine or a sulphur-containing antibiotic having the empirical formula R1.C -1 H 11 N 2 OS, where R1 is C 3 to C 8 alkyl, by cultivating a celesticetinproducing strain of Streptomyces caelestis, e.g. NRRL 2418 (Specification 768,971) in an aqueous nutrient medium to which has been added an (#-alkylthio-α-amino acid of general formula wherein R is C 1 to C 8 alkyl and n is 1 to 4. Desdanine has the formula C 7 H 10 N 3 O. When the terminal alkylthio group of the added α-amino acid is (a) methylthio, desdamethine C 8 H 14 N 2 OS is coproduced; (b) ethylthio, ethesdanine C 9 H 16 N 2 OS is coproduced; (c) propylthio, C 10 H 18 N 2 OS is. coproduced; and (d) butylthio, C 11 H 20 N 2 OS is coproduced. Desdanine may be obtained by heating the aforesaid sulphur-containing antibiotics in dioxane. Desdanine is isolated from the clarified broth by extracting with methylene chloride at pH 6À3 to remove celesticetin, adjusting the pH of the extracted broth to pH 10, if required extracting with methylene chloride to remove ethesdanine, treating the extracted alkaline beer with 1-butanol and concentrating to form a crude. This may be purified by converting it to a water-soluble acid addition salt, e.g. HCl, and regenerating the desdanine by the addition of a base. Desdamethine is recovered from a clarified broth at pH 10 by extraction with nbutanol, re-extracting the butanol extract with dilute hydrochloric acid, adjusting to pH 10, extracting with methylene chloride and concentrating. The antibiotics are effective against gram positive and negative bacteria, and are mono basic, forming salts with acids such as hydrochloric, sulphuric and phosphoric acid. Desdamethine forms a hexafluoroarsenate and hexafluorophosphate which are useful as a parasiticide. Other properties are as follows:-