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Albicidin

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Albicidin
Names
IUPAC name 4-amino]benzoyl]amino]propanoyl]amino]benzoyl]amino]-2-hydroxy-3-methoxybenzoyl]amino]-2-hydroxy-3-methoxybenzoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
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/s1Key: NZSWNNDHPOTJNH-VEJILBAHSA-N
SMILES
  • C/C(=C\C1=CC=C(C=C1)O)/C(=O)NC2=CC=C(C=C2)C(=O)N(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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

As a phytotoxin, it acts by inhibiting the differentiation of chloroplasts. It accomplishes this by inhibiting DNA gyrase, and thereby preventing the replication of chloroplast DNA. 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. Its antibiotic properties were discovered in the early 1980s, when the molecule was isolated and purified from cultures of Xanthomonas albilineans. However, the precise structure of the molecule was only identified in 2015. A laboratory synthesis of albicidin has been developed, and research is currently focused on the design and evaluation of synthetic derivatives of albicidin with improved properties.

References

  1. ^ Kretz, Julian; Kerwat, Dennis; Schubert, Vivien; Grätz, Stefan; Pesic, Alexander; Semsary, Siamak; Cociancich, Stéphane; Royer, Monique; Süssmuth, Roderich D. (2015). "Total Synthesis of Albicidin: A Lead Structure from Xanthomonas albilineansfor Potent Antibacterial Gyrase Inhibitors". Angewandte Chemie International Edition. 54 (6): 1969–1973. doi:10.1002/anie.201409584. PMID 25504839.
  2. Pieretti, Isabelle; Pesic, Alexander; Petras, Daniel; Royer, Monique; Süssmuth, Roderich D.; Cociancich, Stéphane (2015). "What makes Xanthomonas albilineans unique amongst xanthomonads?". Frontiers in Plant Science. 6: 289. doi:10.3389/fpls.2015.00289. PMC 4408752. PMID 25964795.
  3. Hashimi, Saeed M.; Wall, Melisa K.; Smith, Andrew B.; Maxwell, Anthony; Birch, Robert G. (2007). "The Phytotoxin Albicidin is a Novel Inhibitor of DNA Gyrase". Antimicrobial Agents and Chemotherapy. 51 (1): 181–187. doi:10.1128/AAC.00918-06. PMC 1797663. PMID 17074789.
  4. Hashimi, Saeed Mujahid (2019). "Albicidin, a potent DNA gyrase inhibitor with clinical potential". The Journal of Antibiotics. 72 (11): 785–792. doi:10.1038/s41429-019-0228-2. PMID 31451755. S2CID 201644516.
  5. Birch, R. G.; Patil, S. S. (1985). "Preliminary Characterization of an Antibiotic Produced by Xanthomonas albilineans Which Inhibits DNA Synthesis in Escherichia coli". Microbiology. 131 (5): 1069–1075. doi:10.1099/00221287-131-5-1069. PMID 2410547.
  6. Cociancich, Stéphane; Pesic, Alexander; Petras, Daniel; Uhlmann, Stefanie; Kretz, Julian; Schubert, Vivien; Vieweg, Laura; Duplan, Sandrine; Marguerettaz, Mélanie; Noëll, Julie; Pieretti, Isabelle; Hügelland, Manuela; Kemper, Sebastian; Mainz, Andi; Rott, Philippe; Royer, Monique; Süssmuth, Roderich D. (2015). "The gyrase inhibitor albicidin consists of p-aminobenzoic acids and cyanoalanine". Nature Chemical Biology. 11 (3): 195–197. doi:10.1038/nchembio.1734. PMID 25599532.
  7. Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D. (2016). "Synthesis of Albicidin Derivatives: Assessing the Role of N-terminal Acylation on the Antibacterial Activity". ChemMedChem. 11 (17): 1899–1903. doi:10.1002/cmdc.201600231. PMID 27439374. S2CID 5009104.
  8. Grätz, Stefan; Kerwat, Dennis; Kretz, Julian; Von Eckardstein, Leonard; Semsary, Siamak; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, R. D. (2016). "Synthesis and Antimicrobial Activity of Albicidin Derivatives with Variations of the Central Cyanoalanine Building Block". ChemMedChem. 11 (14): 1499–1502. doi:10.1002/cmdc.201600163. PMID 27245621. S2CID 205649206.
  9. "Sweet salvation -- how a sugar cane pathogen is gearing up a new era of antibiotic discovery". Science Daily. January 23, 2023.
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