DESCRIPTIOXS OF ANTIBIOTICS 



289 



34. Wilson, G. B. J. Heredity 12: 251-255, 



1951. 



35. Lewis, C. N. et al. Antibiotics & Chemo- 



therapy 2: 601-609, 1952. 



36. Suzuki, M. and Nagawa, M. J. Pharm. Soc. 



Japan 72: 305-308, 1952. 



37. Williamson, M. et al. J. Biol. Chem. 197: 



763-770, 1952. 



38. Melen, B. Acta Pathol. Microl)iol. Scand. 



3(»: 98-103, 1952. 



39. Smith, G. N. Arch. Biochem. Biophys. 



40: 314-322, 1952. 



40. Dunitz, J. D. J. Am. Chem. Soc. 74: 



995-999, 1952. 



41. Phillips, A. P. J. Am. Chem. Soc. 74: 



6125-6127, 1952. 



42. Collins, R. J. et al. J. Pharm. and Pharma- 



col. 4:693-709,1952. 



43. Day, W. H. et al. Abstr. r24th Meeting 



Am. Chem. Soc. 23A, 1953. 



44. Goldberg, H. S. et al. Food Technol. 7: 



165-166, 1953. 



45. Hemmer, M. L. et al. Antil)iotics & Chem- 



otherapy 3: m^ni, 1953. 



46. Murthy, M. R. V. and Sreenivasaya, Al. 



Nature, London 172: 684-685, 1953. 



47. Kiser, J. S. and deMello, G. C. Proc. 58th 



Ann. Meeting U. S. Livestock Sanitary 

 Assoc. 81-97,1954. 



48. Lasley, J. F. et al. Univ. Missouri Agr. 



Expt. Sta. Bull. 543, 1954. 



49. Pomerat, C. M. and Leake, C. D. Ann. N. 



Y. Acad. Sci. .38: 1110-1124. 1954. 



50. Bozeman, F. M. et al. J. Bacteriol. 



530-536, 1954. 



51. Kirkpatrick, H. C. and Lindner, R. 



Phytopathology 44: 529-533, 1954. 



52. Loosli, C. G. et al. Antibiotics Ann. 474- 



489. 1954-1955. 



53. Klemmer, H. W. et al. Phytopathology 



45: 618-625, 1955. 



54. Gross, J. A. Biochim. et Biophys. Acta 



18: 452-453, 1955. 



55. Rigdon, R. H. et al. Antil)iotics & Chem- 



otherapy 5: 38-44, 1955. 



56. Reutner, T. F. et al. Antil)iotics & Chem- 



otherapy 5:679-711,1955. 



57. Rebstock, M. C. et al. J. Am. Chem. Soc. 



77: 24-26, 1955. 



58. Brunner, L. Zentr. Bakteriol. Parasitenk., 



Orig. 163: 13-30, 1955. 



59. Hahn. F. E. et al. Antibiotics & Chemo- 



therapy 6:531-543,1956. 



60. Hagborg, W. A. F. Can. J. Microbiol. 2: 



80-86, 1956. 



67: 



C. 



61. Woolington, S. S. et al. Antibiotics Ann. 



365-375, 1956-1957. 



62. Thayer, J. U. et al. Antiliiotics Ann. 513- 



517, 1956-1957. 



63. Joel, C. A. and Kornhauser, S. Fertility 



and Sterility 7: 430-439, 1956. 



64. Bernfeld, P. and Inglis, N. R. Proc. Am. 



Assoc. Cancer Research 2: 94, 1956. 



65. Nitta, K. Japan. J. Med. Sci. & Biol. 10: 



277-286, 1957. 



66. Hezebicks, M. M. and Nigg, C. Antil)iotics 



& Chemotherapy 8: 543-560, 1958. 



67. Gale, E. F. In Amino acids and peptides 



with antimetabolic activity. Ciba Foun- 

 dation Symposium. Little, Brown & Co., 

 Boston, 1958, pp. 19-37. 



68. Gentry, R. P. Avian Diseases 2: 76-82, 



1958. 



69. Woodward, T. 1'^. and Wisseman, C. L. 



Chloromycetin (chloramphenicol). Med- 

 ical Encyclopedia Inc., New York, 1958. 



70. Broadbent, D. and Terry, D. A. Nature, 



London 182: 1107-1108, 1958. 



71. Murat, A. M. et al. Appl. Microbiol. 7: 



109-112, 1959. 



72. Lawrence, J. C. Brit. J. Pharmacol. 14: 



168-173, 1959. 



Clilorlelracj cliiie 



Produced by: Streptuinyces atireofaciens (15) 

 and S. sayaniaensis (105). 



SyiK.itiyin.'^: Aureomycin, biomycin, duomycin, 

 fiamycin, s,yntomycin, aureomykoin. (See also 

 tetracyclines.) 



Method of e.rtrartion: lA. Whole broth adjusted 

 to pH 1.4, ammonivmi oxalate and Arquad 16 

 (50 per cent solution in isopropanol) added, pH 

 adjusted to 8.5, and the whole extracted with 

 methyl isobutyl ketone. Water added to extract, 

 and pH adjusted to 0.5. Crystals form on pro- 

 longed stirring. Purified by treatment with so- 

 dium hydrosulfide at pH 1.8 for 10 minutes, then 

 at pH 0.5 for 20 hours (137). Crystallized from hot 

 water on cooling and addition of HCl. Conversion 

 from hydrochloride to base: Substance slurried in 

 dimethylformamide. Addition of NaHCOj gives 

 precipitate. Toluene solution of precipitate azeo- 

 t Topically distilled. Cooling gives precipitate. 

 Recrystallized from benzene (88). IB. Whole 

 broth adjusted to pH 2.9 and filtered. Arquad C 

 (a commercial mixture of alkyl and alkenyltri- 

 methylammonium chlorides, principally dodecyl- 

 trimethylammonium chloride) and calcium chlo- 

 ride are added to filtrate, and pH adjusted to 9.0 

 to precipitate a chlortetracycline-organic base- 



