Structure of virantmycin, a novel antiviral antibiotic

✍ Scribed by Satoshi Ōmura; Akira Nakagawa

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 191 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90497-6

✦ Synopsis

The structure of virantmycin, a novel antiviral antibiotic, isolated from Streptomyces, has been established by chemical and spectroscopic evidences. Virantmycin (L), an antibiotic active against RNA and DNA viruses has been isolated from the fermentation broth of Streptom.vces nitrosporeus". This communication deals with the structural elucidation of 1_. The antibiotic, l_, mp. 59"C, [a]r -0.05" (c 1, CHC13) gave the following spectral data: UV hiiFH 306 nm (E, 8100), IR v,!$ 4 3440 (NH), 3400-2400 (carboxy OH), 1667 (carboxy CO), 1603 cm --I (C=C). The mass spectrum of L showed i4+ ni/z 351 (C1gH26ii03C1) and characteristic fragment peaks at m/z 316 (M+-Cl), 306 (M+-CH20CH3), 270 (M+-CH20CH3-HCl), 1 254 (MC-C7H13) and 83 (C6Hll). The H and 13 C nmr spectra*) of !, and the selective '3CI'H) decoupling experiments exhibited the presence of three-substituted aromatic ring (6H 6.56 d, J= 8.5 Hz, 6H 7.78 d, J=3.0 Hz and 6H 7.82, dd, J=8.5, 3.0 Hz), a carboxyl carbon ("c 171.9), a methine (6H 4.36 t, J=6.0 Hz; 6c 56.2) coupled with a methylene (6H 3.40 dd, J=16.4, 6.0 Hz and 6H 3.08 dd, J=16.4, 6.0 Hz; 6c 33.5), a methoxy methylene (6H 3.46 s; hC. 59.4 for OCH3 and 6H 3.58 s; 6c 74.1 for CH2), two adjacent methylenes (6H 1.6 m; bc 27.8 and 6H 2.0 m; 6c 33.5), a quaternary carbon ("c 58.0) and three methyls (dH 1.60 s; 6c 20.6, 19.9 and 18.4), Rooc24f.py~~3