Ansamycin Explained

Ansamycin should not be confused with Annamycin.

Ansamycins is a family of bacterial secondary metabolites that show antimicrobial activity against many Gram-positive and some Gram-negative bacteria, and includes various compounds, including streptovaricins and rifamycins.[1] In addition, these compounds demonstrate antiviral activity towards bacteriophages and poxviruses.

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Structure

They are named ansamycins (from the Latin ansa, handle) because of their unique structure, which consists of an aromatic moiety bridged by an aliphatic chain.[2] The main difference between various derivatives of ansamycins is the aromatic moiety, which can be a naphthalene ring or a naphthoquinone ring as in rifamycin and the naphthomycins.[3] Another variation consists of benzene or a benzoquinone ring system as in geldanamycin or ansamitocin. Ansamycins were first discovered in 1959 by Sensi et al. from Amycolatopsis mediterranei, an actinomycete bacterium.[4]

Examples

Rifamycins are a subclass of ansamycins with high potency against mycobacteria. This resulted in their widespread use in the treatment of tuberculosis, leprosy, and AIDS-related mycobacterial infections.[5] Since then various analogues have been isolated from other prokaryotes.

Notes and References

  1. Wehrli, W. . Staehelin, M. . Bacteriological Reviews. Actions of the rifamycins . 35 . 3 . 290–309 . 1971 . 5001420 . 378391. 10.1128/MMBR.35.3.290-309.1971 .
  2. Prelog, V. . Oppolzer, W. . Rifamycins. 4. Ansamycins, a novel class of microbial metabolism products . Helvetica Chimica Acta . 56 . 1179–1187 . 1973 . 7 . 10.1002/hlca.19730560716. 4148590 .
  3. Balerna, M. . Keller-Schierlein, W. . Martius, C. . Wolf, H. . Zähner, H. . Archiv für Mikrobiologie. Metabolic products of microorganisms. 72. Naphthomycin, an antimetabolite of vitamin K . 65 . 303–17 . 1969 . 4988744 . 4 . 10.1007/bf00412210. 31145406 .
  4. Sensi, P. . Margalith, P. . Timbal, M. T. . Il Farmaco, Edizione Scientifica. Rifomycin, a new antibiotic; preliminary report . 14 . 2 . 146–7 . 1959 . 13639988.
  5. Floss, H. G. . Yu, T. . Current Opinion in Chemical Biology. Lessons from the rifamycin biosynthetic gene cluster . 3 . 592–7 . 1999 . 10.1016/S1367-5931(99)00014-9 . 10508670 . 5.