Albicidin

Albicidin is an antibiotic and phytotoxic molecule produced by the bacterium Xanthomonas albilineans which infects sugarcane causing leaf scald.^[1]

Quick facts Names, Identifiers ...

Albicidin

Names
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
CAS Number	96955-97-4
3D model (JSmol)	Interactive image
ChemSpider	32821621
PubChem CID	78322514
InChI InChI=1S/C44H38N6O12/c1-23(22-24-4-14-29(51)15-5-24)39(54)46-27-10-6-26(7-11-27)41(56)50-34(20-21-45)43(58)47-28-12-8-25(9-13-28)40(55)48-32-18-16-30(35(52)37(32)61-2)42(57)49-33-19-17-31(44(59)60)36(53)38(33)62-3/h4-19,22,34,51-53H,20H2,1-3H3,(H,46,54)(H,47,58)(H,48,55)(H,49,57)(H,50,56)(H,59,60)/b23-22+/t34-/m0/s1 Key: NZSWNNDHPOTJNH-VEJILBAHSA-N
SMILES C/C(=C\C1=CC=C(C=C1)O)/C(=O)NC2=CC=C(C=C2)C(=O)N[C@@H](CC#N)C(=O)NC3=CC=C(C=C3)C(=O)NC4=C(C(=C(C=C4)C(=O)NC5=C(C(=C(C=C5)C(=O)O)O)OC)O)OC
Properties
Chemical formula	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). Infobox references

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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 drug-like properties.^{[7][8][9][10]}