Ansamycin
From Wikipedia, the free encyclopedia
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.
[edit] Structure
They are named ansamycins—ansa from the Latin for 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 naphthomycin [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]
[edit] Examples
Rifamycins are a subclass of ansamycins with high potency against mycobacterial activity. This resulted in their wide use in the treatment of tuberculosis, leprosy, and AIDS-related mycobacterial infections.[5] Since then various analogues have been isolated from other prokaryotes.
[edit] References
- ^ Wehrli, W.; Staehelin, M. (1971). "Actions of the rifamycins". Bacteriol. Rev. 35: 290.
- ^ Prelog, V.; Oppolzer, W. (1973). "Rifamycins. 4. Ansamycins, a novel class of microbial metabolism products". Helv. Chim. Acta. 56: 2279.
- ^ 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: 303.
- ^ Sensi, P.; Margalith, P.; Timbal, M. T. (1959). "Rifomycin, a new antibiotic; preliminary report". Ed. Sci. 14: 146.
- ^ Floss, H. G.; Yu, T. (1999). "Lessons from the rifamycin biosynthetic gene cluster". Curr. Opin. Chem. Biol. 3: 592. doi:.
