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United States Patent [1113,616,243 United. States Patent [1113,616,243 [72] Inventors Shohei Kawaji [51] Int. Cl ........................................ .. Cl2d 9/00 Tokyo; _ [50] Field of Search .......................................... .. 195/80 Toyoaki Kawasaki, Tokyo; Masao Murase, _ Kawasaki-shi; Shunzo Fukatsu, Tokyo; [56] References Clted Masahiro Abe, Kawasaki-shi; Yoshihisa UNITED STATES PATENTS £10818,amoru TgkywkTaéslf uzu i, o o lhlo, ama-s Yolilqhgflna-slgi; I; asa lro 2,936,307 5/1960 Johnson et al .............. .. 195/80 x Ueda, Kawasaki-shi; Hamao Umezawa, FOREIGN PATENTS [21] APPL NO- Tokyo,751,478 8“ of Japan Primary8,695 Examiner—Joseph 1961 Japan M. ......................... Golian .. [22] Filed Aug. 9, 1968 Attorney-Mason, Fenwick & Lawrence [45] Patented Oct. 26, 1971 [73] Assignee Meiji Seika Kaisha, Ltd. Tokyo, Japan ABSTRACT: This invention relates to processes for the [54] PROCESS FOR THE PRODUCTION OF AN production of an antibiotic substance 2’-amino-2'-deoxy ANTIBIOTIC SUBSTANCE 2'-AMINO-2 '-DEOXY kanamyein in higher yield. More particularly, this invention KANAMYCIN IN HIGHER YIELD relates to the processes for the production of 2’-amino-2' 1 Claim, 2 Drawing Figs. deoxy-kanamycin by fermentation using mutants of Strepto myces kanamyceticus identi?ed as ATCC2 l 259, ATCC21260, [52] U.S. Cl ....................... .f ............................. .. 195/80 ATCCZI I61 and ATCC2I268. PATENTEunm 26 I9?! ' 3,616,243 SHEET 10F 2 " 260280360320340mp LENGTHWAVE' FIG.I 200 Q. ‘0. 12 1.0- o o 0.2- ABSORBANCE PATENTEDUU 261971 3.616.243 SHEET 2 UF 2 $-53mmmznzgss N61. 00.00.0m00.:00$00.200300.9ooLowooww00mm0.0.800m.00mm000*» PERCENT TRANSMISSION 3,616,243 1 2 PROCESS FOR THE PRODUCTION OF AN ANTIBIOTIC According to the present invention, therefore, we provide a SUBSTANCE 2'-AMINO-2 '-DEOXY-KANAMYCIN IN process for the production of 2'-amino-2'-deoxy-kanamycin HIGHER YIELD in higher yield, which comprises cultivating a mutant of 2'-Amino-2'-deoxy-kanamycin is effective in inhibiting the Streptomyces kanamyceticus which intrinsically exhibits the growth of Gram-positive, Gram-negative and acid-fast bac greater capability to produce 2’-amino-2'-deoxy-kanamycin, teria such as Staphylococcus, Pseudomonas, Salmonella, under aerobic conditions in a usual culture medium contain Shigella and Mycobacterium as well as pathogenic bacteria ing the ordinary carbon sources and nitrogen sources, until 2' which are resistant to the known antibiotics and synthetic amino-2’-deoxy-kanamycin accumulates in a signi?cant chemotherapeutic agents. This 2'-amino-2'-deoxy-kanamycin amount in ‘the culture, and then recovering said antibiotic is substantially of very much low toxicity and particularly of from the culture. little ototoxicity, and it exhibits a useful therapeutic effect on As embodiments of the process of the present invention, the infections of Gram-positive, Gram-negative and acid-fast there are also provided a process for the production of 2' bacteria in human beings and animals. amino-2'-deoxy-kanamycin in a higher yield, which comprises 2'-Amino-2’-deoxy-kanamycin has the empirical formula cultivating the mutant A-4—6,3AG, 18-8 or 19-2 of Strepto CmHgNsOipHgQjlld may be represented by the structural myces kanamyceticus under aerobic conditions in a usual cul formula: ture medium containing carbohydrate and nitrogenous nutrient until the 2'-amlno-2'-deoxy-kanamycin accumulates in a signi?cant amount in the culture, and then recovering said antibiotic from the culture. 20 4v in the process of the present invention, the cultivation may 2. so a generally be carried out in the usual manner as in the ordinary methods of cultivating the known actinomycetes. The culture as 3' 2 o 6' medium containing known kinds of nutritional sources for ac - on an 25 tinomycetes are useful for the production of 2'-amino-2' 6 OH 1' 5, 2 2 deoxy-kanamycin. Thus, the culture medium may contain the 0 sources of carbon such as starch, sucrose, maltose, glucose and glycerol etc. and the sources of nitrogen such as soybean Hall meal, soluble vegetable proteins, corn steep liquor, peptone, '30 meat extract, nitrates and ammonium salts. The culture medi 3 N“2 um may also contain other appropriate inorganic salts such as NaCl, MgSO, and such a material which will promote the growth of Streptamyces kanamyceticus, if necessary. in investigating the commercial production of kanamycin A For the production of 2'-amino-2'-deoxy-kanamycin, the by the fermentation, we have, found that the known natural 35 cultivation on solid medium is possible, but for the production strains such as strain 0-4-1 of Streptomyces kanamyceticus in large quantity it is better to carry out the cultivation in a which have been used up to now for the commercial produc liquid medium under aerobic conditions. For the production tion of kanamycin A usually can produce and accumulate of the antibiotic on a large scale it is much more preferable to kanamycin A in a very much larger amount than 2’-amino-2' employ a method of deep aerated submerged cultivation. it is deoxy-kanamycin in the culture. 40 possible to use the shake-cultivation and the aerated agitated As result of our further investigations, we have found that cultivation in a liquid medium. The cultivation temperature the proportion of 2’-amino-2’-deoxy-kanamycin produced usually may be between 25° and 35° C. and preferably at a and accumulated in the culture may be improved remarkably temperature of 28° C. or in the vicinity thereof. It has been and may be recovered therefrom in higher yield when some found that the amount of 2'-amino-2’-deoxy-kanamycin accu new mutants of Streptomyces kanamyceticus are cultured in 45 mulating in the culture becomes maximum at the end of 3 to 7 the known manner using an ordinary culture medium which days after the beginning of the cultivation. are conventionally employed for the cultivation. Thus, we 2’-Amino-2’-deoxy-kanamycin which has accumulated in have further discovered that some new mutants of Strepto the culture may be recovered therefrom by any one of the m yces kanamyceticus which we have now derived from a typi known method of using ion-exchange resins, the method of ex cal natural strain 0-4-1 of Strepromyces kanamyceticus can ex tracting with organic solvents and the method of using a hibit a higher ability to produce 2'-amino-2'-deoxy-kana precipitating agent which are usually employed for the puri? mycin than the parent natural strain 0-4-1, when they are cul cation of the known water-soluble, basic antibiotics. For the tivated in the known culture medium. commercial production of 2'-amino-2'-deoxy-kanamycin, it is These new mutants having intrinsically the greater capabili preferred to recover this by a method of adsorption and elu ty to produce 2'-amino-2'-deoxy-kanamycin have been ob tion with an ion exchanger, preferably carboxylic acid type ca tained by treating the known, natural strain 0-4-1 of Strepto tion-exchange resin, or by a method of extraction with an or myces kanamyceticus with a mutation agent, namely nitrogen ganic solvent containing an appropriate carrier such as mustard or irradiation of ultraviolet rays and subjecting the paratoluene sulfonic acid or lauric acid. For instance, 2' surviving mycelia or spores to special screening. 60 amino-2'-deoxy-kanamycin may be recovered by ?ltering off These new mutants which intrinsically have the greater the solids such as mycelium cake from the fermented broth capability to produce 2'-amino~2’-deoxy-kanamycin include containing 2'-amino-2'-deoxy-kanamycin, subjecting the ?l four types of mutants which have been given the laboratory trate to an adsorption treatment with Amberlite lRC-SO (a re designations A-4-6, 3A6, 18-8 and 19-2, respectively. These gistered Trade Name of an ion-exchange resin as produced by new mutants each have little or no ability to utilize xylose, and 65 Rohm & Haas Co., U.S.A.), eluting with aqueous ammonia, they are distinguishable from the parent strain 0-4-1 which collecting and concentrating the active fractions, subjecting has a greater capability to utilize xylose. the concentrated fraction to chromatographic separation with Variation or mutation of Streptomyces kanamyceticus is Dowex 1X2 (a registered Trade Name of an ion-exchange naturally expected since such is a common property of an ac resin as produced by Dow Chemical Co., U.S.A.), collecting tinomyces. Therefore, when any known strain of Streptomyces 70 and concentrating the active fractions. The concentrated frac kanamyceticus is treated with a known mutation agent such as tion is again subjected to a chromatographic separation by ad nitrogen mustard, it may be expected thatI in addition to the sorbing on Amberlite CG-SO and gradient eluting with water above-mentioned mutants A-4-6,3 AG, 18-8 and 19-2, there aqueous ammonia. A single fraction containing an active com are obtained other mutants which intrinsically exhibit the pound, that is, 2’-amino~2'-deoxy-kanamycin may be ob greater capability to produce 2'-amino-2'-deoxy-kanamycin. 75 tained. This fraction is freeze-dried and the resulting powder is 3,616,243 3 crystallized from water-dimethyl formamide to yield the Saccharomyces cerevisiae crystals of 2'-amino-2'-deoxy-kanamycin. _ 1AM 4626 500 Shigella ?exneri EW 10 2a 0.039 2’-Amino-2‘-deoxy-kanamycin may be obtained in the form Streptococcus faecalis of colorless needlelike crystals having a melting point of ATCC 8043 15.6 183°-186° C. basic and soluble in water, aqueous methanol, Staphylococcus aureus aqueous ethanol, aqueous acetone but insoluble in absolute 209? (resistant to streptomycin) 2.5 methanol, absolute ethanol, ethyl acetate, butyl acetate, ethel Staphylococcus aureus ether, chloroform and benzene, giving ‘positive reaction to nin 209? (resistant to hydrin, Elson-Morgan and Molisch reagents but negative reac erythromycin) 0.31 Escherichia coli K-12CS-2 0.31 tion to Sakaguchi, Tollens, Fehling, Millon and Benedict re Escherichia coli K-lZCS agents, and an aqueous 1 percent solution of this substance 2(resistant to shows a speci?c rotation [0111)”: plus 1 18"‘.
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