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Structure of hygromycin B, an antibiotic from Streptomyces hygroscopicus; The use of CMR. spectra in structure determination, I

✍ Scribed by N. Neuss; K. F. Koch; B. B. Molloy; W. Day; L. L. Huckstep; D. E. Dorman; J. D. Roberts


Publisher
John Wiley and Sons
Year
1970
Tongue
German
Weight
394 KB
Volume
53
Category
Article
ISSN
0018-019X

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✦ Synopsis


recrystallized from 15 ml of hot absolute ethanol. After standing overnight in refrigerator, 0.85 g of colorless hysoamine, m.p. 183-186", were obtained. [a]g = -k 39.8" (c = 2, H,O). C,H1,N,O, Calc. M + 176.1189 Found M + 176.12056) Preparation of N-Methyl-deoxystreptamine from Destomycin A . This amino cyclitol was prepared analogously t o hyosamine; however, starting from 5 g of crude destomycin A, only 210 mg of crystalline, chromatographically impure material were obtained. This was first chroma tographed on Bio-Rad resin (150 g, Dowex, 200400 mesh, OH cycle) using water as eluent yielding 180 mg of still impure amino cyclitol [a12 = -26.6" (H,O) (TLC., Merck Cellulose Plates, MeOH--CHCl,NH,OH 3 : 1 : 2 vol.). This material was rechromatographed on 25 g of cellulose (Schleicher & Schuell, grade 286) using MeOH-CHC13-NH,OH 3 : 1 : 2 vol. solvent mixture. Fractions of 15 ml were collected and examined by TLC. Fractions No. 1-7 were discarded. Fraction No. 8 gave 119 mg of crystalline, chromatographically homogeneous amino cyclitol melting a t 120-126", then resolidifying and melting at 160-162". [a12 = -31,l" Calc. M+ 176.1189 Found 176.11606) Preparation of Destomic Acid from Hygromycin B. This acid was prepared analogously to procedure described for its isolation from destomycin A [3]. The material was identical (IR., NMR., X-ray powder data and TLC.) with an authentic sample from the Japanese investigators4).

M.p. 207-209". [a12 = + 5.3" (c = 2, H,O).


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