albicidin
{{Chembox
| ImageFile = Albicidine.svg
| ImageSize = 250px
| IUPACName = 4-
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 96955-97-4
| ChemSpiderID = 32821621
| PubChem = 78322514
| 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
| StdInChI=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
| StdInChIKey = NZSWNNDHPOTJNH-VEJILBAHSA-N
}}
| Section2 = {{Chembox Properties
| C = 44 | H = 38 | N = 6 | O = 12
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
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| Section3 = {{Chembox Hazards
| MainHazards =
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Albicidin is an antibiotic and phytotoxic molecule produced by the bacterium Xanthomonas albilineans which infects sugarcane causing leaf scald.{{Cite journal | doi = 10.1002/anie.201409584 | title = Total Synthesis of Albicidin: A Lead Structure from Xanthomonas albilineansfor Potent Antibacterial Gyrase Inhibitors | year = 2015 | last1 = Kretz | first1 = Julian | last2 = Kerwat | first2 = Dennis | last3 = Schubert | first3 = Vivien | last4 = Grätz | first4 = Stefan | last5 = Pesic | first5 = Alexander | last6 = Semsary | first6 = Siamak | last7 = Cociancich | first7 = Stéphane | last8 = Royer | first8 = Monique | last9 = Süssmuth | first9 = Roderich D. | journal = Angewandte Chemie International Edition | volume = 54 | issue = 6 | pages = 1969–1973 | pmid = 25504839 | doi-access = free }}
As a phytotoxin, it acts by inhibiting the differentiation of chloroplasts.{{Cite journal | doi = 10.3389/fpls.2015.00289 | doi-access = free | title = What makes Xanthomonas albilineans unique amongst xanthomonads? | year = 2015 | last1 = Pieretti | first1 = Isabelle | last2 = Pesic | first2 = Alexander | last3 = Petras | first3 = Daniel | last4 = Royer | first4 = Monique | last5 = Süssmuth | first5 = Roderich D. | last6 = Cociancich | first6 = Stéphane | journal = Frontiers in Plant Science | volume = 6 | page = 289 | pmid = 25964795 | pmc = 4408752 | bibcode = 2015FrPS....6..289P }} It accomplishes this by inhibiting DNA gyrase, and thereby preventing the replication of chloroplast DNA.{{cite journal | doi = 10.1128/AAC.00918-06 | title = The Phytotoxin Albicidin is a Novel Inhibitor of DNA Gyrase | year = 2007 | last1 = Hashimi | first1 = Saeed M. | last2 = Wall | first2 = Melisa K. | last3 = Smith | first3 = Andrew B. | last4 = Maxwell | first4 = Anthony | last5 = Birch | first5 = Robert G. | journal = Antimicrobial Agents and Chemotherapy | volume = 51 | issue = 1 | pages = 181–187 | pmid = 17074789 | pmc = 1797663 }} 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.{{cite journal | doi = 10.1038/s41429-019-0228-2 | title = Albicidin, a potent DNA gyrase inhibitor with clinical potential | year = 2019 | last1 = Hashimi | first1 = Saeed Mujahid | journal = The Journal of Antibiotics | volume = 72 | issue = 11 | pages = 785–792 | pmid = 31451755 | s2cid = 201644516 }} Its antibiotic properties were discovered in the early 1980s, when the molecule was isolated and purified from cultures of Xanthomonas albilineans.{{Cite journal | doi = 10.1099/00221287-131-5-1069 | title = Preliminary Characterization of an Antibiotic Produced by Xanthomonas albilineans Which Inhibits DNA Synthesis in Escherichia coli | year = 1985 | last1 = Birch | first1 = R. G. | last2 = Patil | first2 = S. S. | journal = Microbiology | volume = 131 | issue = 5 | pages = 1069–1075 | pmid = 2410547 | doi-access = free }} However, the precise structure of the molecule was only identified in 2015.{{cite journal | doi = 10.1038/nchembio.1734| title = The gyrase inhibitor albicidin consists of p-aminobenzoic acids and cyanoalanine| year = 2015| last1 = Cociancich| first1 = Stéphane| last2 = Pesic| first2 = Alexander| last3 = Petras| first3 = Daniel| last4 = Uhlmann| first4 = Stefanie| last5 = Kretz| first5 = Julian| last6 = Schubert| first6 = Vivien| last7 = Vieweg| first7 = Laura| last8 = Duplan| first8 = Sandrine| last9 = Marguerettaz| first9 = Mélanie| last10 = Noëll| first10 = Julie| last11 = Pieretti| first11 = Isabelle| last12 = Hügelland| first12 = Manuela| last13 = Kemper| first13 = Sebastian| last14 = Mainz| first14 = Andi| last15 = Rott| first15 = Philippe| last16 = Royer| first16 = Monique| last17 = Süssmuth| first17 = Roderich D.| journal = Nature Chemical Biology| volume = 11| issue = 3| pages = 195–197| pmid = 25599532}} 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.{{cite journal | doi = 10.1002/cmdc.201600231 | title = Synthesis of Albicidin Derivatives: Assessing the Role of N-terminal Acylation on the Antibacterial Activity | year = 2016 | last1 = Kerwat | first1 = Dennis | last2 = Grätz | first2 = Stefan | last3 = Kretz | first3 = Julian | last4 = Seidel | first4 = Maria | last5 = Kunert | first5 = Maria | last6 = Weston | first6 = John B. | last7 = Süssmuth | first7 = Roderich D. | journal = ChemMedChem | volume = 11 | issue = 17 | pages = 1899–1903 | pmid = 27439374 | s2cid = 5009104 }}{{cite journal | doi = 10.1002/cmdc.201600163 | title = Synthesis and Antimicrobial Activity of Albicidin Derivatives with Variations of the Central Cyanoalanine Building Block | year = 2016 | last1 = Grätz | first1 = Stefan | last2 = Kerwat | first2 = Dennis | last3 = Kretz | first3 = Julian | last4 = Von Eckardstein | first4 = Leonard | last5 = Semsary | first5 = Siamak | last6 = Seidel | first6 = Maria | last7 = Kunert | first7 = Maria | last8 = Weston | first8 = John B. | last9 = Süssmuth | first9 = R. D. | journal = ChemMedChem | volume = 11 | issue = 14 | pages = 1499–1502 | pmid = 27245621 | s2cid = 205649206 }}{{cite web | url = https://www.sciencedaily.com/releases/2023/01/230123123253.htm | title = Sweet salvation -- how a sugar cane pathogen is gearing up a new era of antibiotic discovery | date = January 23, 2023 | publisher = Science Daily }}