Partial structure of antibiotic LL-AC541

✍ Scribed by Donald B. Borders; W.K. Hausmann; Eugene R. Wetzel; E.L. Patterson

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 252 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89719-7

✦ Synopsis

In the antibiotic program conducted in our laboratories, a strain of Streptomyces hygroscopicue isolated from soil was found to produce e water-soluble, strongly basic entibiotic active against gram-negative end gram-positive bacteria. The antibiotic, called LL-AC541, was isolated by carbon and ion-exchange chromatography es en amorphous hydrochloride salt (Found: C, 35.68; Ii, 6.04; N, 18.58; 0, 24.35; Cl, l2.31), [G 'z -58' (2 1.09, water), mp 200-215' d, no absorption from 220 w to 400 q.' Hydrolysis of the antibiotic with 3 E hydrochloric acid at reflux temperature for 5 hr yielded glyclne, etreptolidine, ammonia, carbon dioxide, formic acid, a reducing compound (I), end a very basic compound (II). Streptolidlne, isolated a8 the crystalline dihydrochlorldr Salt, rtp.~2l5~ d, [u] 'i +55.3 (5 1.01, water), was identified by direct ccmparleon with an authentic sample obtained by hydrolysis of streptothricin. 2 Compound I was isolated from the hydrolyeete by chromatography on cellulose and then on Dowex 5oU-X8 (Ii' form) as a cryatalU.ne hydrochloride salt, C 7H151i05.HCl (Found: C, 36.48; H, 6.89; N, 6.10), mpul55' d, [ti] 'z +39' initial (extrapolated), -22' final (2 0.785, water).

It has been tentatively identified as N-methyl -u-D-gulosemine from the following evidence.