Polyene antimycotic
From Wikipedia, the free encyclopedia
Polyene antimycotics, sometimes referred to as polyene antibiotics, are a class of antimicrobial polyene compounds that target fungi.[1] These polyene antimycotics are typically obtained from some species of Streptomyces bacteria. The polyenes bind to ergosterol in the fungal cell membrane and promote leakiness which may contribute to fungal cell death. Amphotericin B, nystatin, and natamycin are examples of polyene antimycotics.
[edit] Structures
Their chemical structures feature a large ring of atoms (essentially a cyclic ester ring) containing multiple conjugated carbon-carbon double bonds (hence polyene) on one side of the ring and multiple hydroxyl groups bonded to the other side of the ring. Their structures also often have a d-mycosamine (a type of amino-glycoside) group bonded to the molecule.[2] The series of conjugated double bonds typically absorbs strongly in the ultraviolet-visible region of the electromagnetic spectrum, often resulting in the polyene antibiotics having a yellow color.
Chemical structure of
Amphotericin B. Amphotericin B is an example of a yellow-colored polyene antimycotic agent. Note the alternating double and single bonds in the center and the mycosamine group in the bottom right corner.
Chemical structure of
Natamycin, sometimes called pimaricin.
[edit] Biosynthesis
The natural route to synthesis includes polyketide synthase components.[3]
[edit] Other examples of polyenes
[edit] References
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