Albicidin
Chemical compound / From Wikipedia, the free encyclopedia
Albicidin is an antibiotic and phytotoxic molecule produced by the bacterium Xanthomonas albilineans which infects sugarcane causing leaf scald.[1]
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Names | |
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IUPAC name
4-[[4-[[4-[[(2S)-3-cyano-2-[[4-[[(E)-3-(4-hydroxyphenyl)-2-methylprop-2-enoyl]amino]benzoyl]amino]propanoyl]amino]benzoyl]amino]-2-hydroxy-3-methoxybenzoyl]amino]-2-hydroxy-3-methoxybenzoic acid | |
Identifiers | |
3D model (JSmol) |
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PubChem CID |
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Properties | |
C44H38N6O12 | |
Molar mass | 842.818 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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As a phytotoxin, it acts by inhibiting the differentiation of chloroplasts.[2] It accomplishes this by inhibiting DNA gyrase, and thereby preventing the replication of chloroplast DNA.[3] As such it plays a major role in leaf scald disease.
As a DNA gyrase inhibitor, albicindin also has potential therapeutic use as an antibiotic.[4] Its antibiotic properties were discovered in the early 1980s, when the molecule was isolated and purified from cultures of Xanthomonas albilineans.[5] However, the precise structure of the molecule was only identified in 2015.[6] A laboratory synthesis of albicidin has been developed,[1] and research is currently focused on the design and evaluation of synthetic derivatives of albicidin with improved properties.[7][8][9]