Chemistry of the Ansamycin Antibiotics
The ansamycins constitute a class of antibiotics characterized by an aliphatic bridge linking two non-adjacent positions of an aromatic nucleus. The name, originally suggested by Prelog , is derived from the term “ansa compounds” coined by Lüttringhaus in
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I. Intraductian 0 00 00 . . • . . . • . . • . . . . . . . . . . . . . . . . . . . . • . • . . • . • . . • . . • . • . • . . • • • • 232 II. Structures af the Naturally Occurring Ansamycins ..... 0.. 0.•.. 0.. 0 . • . . . . • . . Ao Streptavaricins 0 •••• 0 • 0 0 . 0 • 0 0 . 0 •. 0 • 0 00 0 0 . 0 •. 0 • 0 00...•• 0 • 0 •• 0 •••••• 0 00 B. Rifamycins 0 •• 0 .•.•.••.• 0...•.. 0 •. 0 •• 0.•....•.. 0....•.•..•.....•••.• C. Haiamieins 0 • 0 0 • 0 0 • 0 • 0 • 0 00 0 0 •. 0 .• 0 • 0 • 0 0 •.•• 0 • 00 00 • 0 •.•• 0 0• 0••..•. 0 • 0 D. Talypamycins 00 ••••• 0 ••• 0 ••.••• 0 •• 0•••••.•. 0 0. 0. 0 0 •.•. 0 .•• 0. 0 •.. 0 00 0 E. Naphthamycin 0 . 0 • 0 0 • 0 00 •.••.•.. 0 .• 0 . 0. 0 •. 0.. 0. 0..... 0 . 0 . . . . • . . . . • . • F. Geldanamycin ...... 0 •• o0 •••••••• 0. 0 0. 0 •... 0. 0. 0 •••. 0. 0 0. 0 •• 0 •.•. 0 00 G. Maytansinaids .............................. 0 • 0 . • • . . • . . • • • • • • • • . • . • • H. Three-dimensianal Structures ... 0 0 •• 0 00 0 •• 0 •. 0 •• 0 • 0 •. 0 . 0 •• 0• 0 • 0 •.•• 0 0 III. Reactians af the Ansamycins . 0 00 0 •.•• 0• 0 •••••.•. 0 • 0 ••••.••••••••• 0 •.... 0 • A. Streptavaricins .. 0 •. 0 0 • 0 •• 00 ...•. 0 . 0 0. 0 0 0..... 0. . . . • . • . . . . . . . • . . . • • . • I. Degradatians .... 00 • 0 • 0 0..•..• 0 • 0 0 • 0 ••••••• 0 ••••.••.••••••.••. 0 00 • 2. Derivatizatians ........ 0 •..•..•.••. 0....... 0 . . . . . . . . . • . . . . • . • . • • • • B. Rifamycins . 0 ••.•••. 0 • 0 •. 0 •. 0..•..• 0 •• 0 •.•.••••• 0 0 • 0 • • • • • • • • • • • . • . . • I. Degradatians .... 0 • 0 • 0 • 0 •• 0 • 0 0 •• 0 00 0 •. 0 •. 0 • 0•• 0 •.••.•• 0 . 0• • . • . • • • • 20 Derivatizatians . 00 00 • 0 •••.... 0 • 0 •••.••.•. 0 00 • 0 ••. 0 . 0 00 • 0 •. 0 •. 0 0 . 0 C. Haiamieins 0 0 • 0 •.•••• 0 0• 0 • 0 ... 0 . 0 • 0•• 0••..•••• 0 0 •..•.•• 0 . 0 •• 0 •••.• 0 • D. Talypamycin .......... 0. 0 •••••.••••.••.••••.• 0......... 0 . 0 . . . . . . . . . I. Degradatians .... 0 00 0 ••••.•.. 0 • 0 •••••.... 0 • 0 • 0 •..•.• 0 00 • 0 •. 0 •. 0 0 • 0 2. Derivatizatians . 0 .. 0 . • . . • . • . . • . . . • • . • . • • • ••• 0 •.•.••••••.••.•. 0 . . • E. Naphthamycin 0 ••. 0 0 • 0 00 0 ••••..•.• 00 ••.•••.•••••.•..•. 0 • 0 • 0 0 • • • . • • • • F. Geldanamycin 0 •.•. 0 0. 0 .• 0•....•.• 0.•.. 0.... 0...................... I. Degradatians . 0 •• 0 •.•.••.•••. 0 ..•• 0 •••.•.•••• 0 0... 0 . 0 00 • 0 0 •.•• 0 0 • • 2. Derivatizatians . 0 .. 0....•....•..•...•... 0 ••.••.••••••••••••.•.. 0 . 0
G. Cimino et al., Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products © Springer-Verlag Wien 1976
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K. L. RINEHART, JR., and L. S. SHIELD:
232
G. Maytansinoids H. Conclusions Regarding Bioactivity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 280 IV. Physicai Properties of the Ansamycins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . A. Ultravio1et, Rotatory, Infrared Spectra . . . . . . . . . .
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