Ansamycin

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Not to be confused with Annamycin. ‹See Tfd›
Structure of geldanamycin, one of the benzoquinone ansamycins.

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

Structure[edit]

They are named ansamycins (from the Latin ansa, handle) because of their unique structure, which comprises 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 comprises 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.[4]

Examples[edit]

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.

References[edit]

  1. ^ Wehrli, W.; Staehelin, M. (1971). "Actions of the rifamycins". Bacteriol. Rev. 35 (3): 290. PMC 378391. PMID 5001420. 
  2. ^ Prelog, V.; Oppolzer, W. (1973). "Rifamycins. 4. Ansamycins, a novel class of microbial metabolism products". Helv. Chim. Acta. 56: 2279. 
  3. ^ Balerna, M.; Keller-Schierlein, W.; Martius, C.; Wolf, H.; Zähner, H. (1969). "Metabolic products of microorganisms. 72. Naphthomycin, an antimetabolite of vitamin K". Arch. Mikrobiol. 65 (4): 303. doi:10.1007/bf00412210. PMID 4988744. 
  4. ^ Sensi, P.; Margalith, P.; Timbal, M. T. (1959). "Rifomycin, a new antibiotic; preliminary report". Ed. Sci. 14: 146. 
  5. ^ Floss, H. G.; Yu, T. (1999). "Lessons from the rifamycin biosynthetic gene cluster". Curr. Opin. Chem. Biol. 3 (5): 592. doi:10.1016/S1367-5931(99)00014-9. PMID 10508670.