[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/dihydromaltophilin-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki40\/dihydromaltophilin-wikipedia\/","headline":"Dihydromaltophilin – Wikipedia","name":"Dihydromaltophilin – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia Dihydromaltophilin Names IUPAC name after-content-x4 (3E,5S,7S,8R,9S,10S,11S,13R,15R,16S,18Z)-11-Ethyl-7,24,28-trihydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.05,16.08,15.09,13]octacosa-1(28),3,18-triene-2,20,27-trione after-content-x4 Systematic IUPAC name (3E,5S,7S,8R,9S,13R,15R,16S)-11-Ethyl-7,28-dihydroxy-8,10-dimethyl-21,26-diazapentacyclo[23.2.1.05,16.08,15.09,13]octacosa-1(28),3-diene-2,27-dione Other names Heat-Stable","datePublished":"2016-06-11","dateModified":"2016-06-11","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki40\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/e\/ee\/Heat-Stable_Anti-fungal_Factor_%28Dihydromaltophilin%29.svg\/220px-Heat-Stable_Anti-fungal_Factor_%28Dihydromaltophilin%29.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/e\/ee\/Heat-Stable_Anti-fungal_Factor_%28Dihydromaltophilin%29.svg\/220px-Heat-Stable_Anti-fungal_Factor_%28Dihydromaltophilin%29.svg.png","height":"125","width":"220"},"url":"https:\/\/wiki.edu.vn\/en\/wiki40\/dihydromaltophilin-wikipedia\/","about":["Wiki"],"wordCount":3819,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopediaDihydromaltophilinNamesIUPAC name       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4(3E,5S,7S,8R,9S,10S,11S,13R,15R,16S,18Z)-11-Ethyl-7,24,28-trihydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.05,16.08,15.09,13]octacosa-1(28),3,18-triene-2,20,27-trione       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Systematic IUPAC name(3E,5S,7S,8R,9S,13R,15R,16S)-11-Ethyl-7,28-dihydroxy-8,10-dimethyl-21,26-diazapentacyclo[23.2.1.05,16.08,15.09,13]octacosa-1(28),3-diene-2,27-dioneOther namesHeat-Stable Anti-fungal Factor (HSAF)       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4IdentifiersChemSpiderInChI=1S\/C29H40N2O6\/c1-3-15-11-17-12-19-18-5-4-6-23(35)30-10-9-21(33)27-28(36)26(29(37)31-27)20(32)8-7-16(18)13-22(34)25(19)24(17)14(15)2\/h4,6-8,14-19,21-22,24-25,27,32-34H,3,5,9-13H2,1-2H3,(H,30,35)(H,31,37)\/b6-4-,8-7+,26-20?\/t14-,15-,16+,17+,18-,19+,21?,22-,24+,25-,27?\/m0\/s1Key:\u00a0VYCDZNHSSDXACI-SGXRADKASA-NCC[C@H]1C[C@@H]2C[C@@H]3[C@H]4C\/C=CC(=O)NCCC(C5C(=C(C(=O)\/C=C\/[C@@H]4C[C@@H]([C@H]3[C@@H]2[C@H]1C)O)C(=O)N5)O)OPropertiesC29H40N2O6Molar mass512.647\u00a0g\u00b7mol\u22121Except where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compoundDihydromaltophilin, or heat stable anti-fungal factor (HSAF), is a secondary metabolite of Streptomyces sp. and Lysobacter enzymogenes.[1][2][3] HSAF is a polycyclic tetramate lactam containing a single tetramic acid unit and a 5,5,6-tricyclic system. HSAF has been shown to have anti-fungal activity mediated through the disruption of the biosynthesis of Sphingolipid’s by targeting a ceramide synthase unique to fungi.[4][5]Biosynthesis[edit]The backbone of HSAF is formed through a hybrid PKS-NRPS cluster containing one nonribosomal peptide synthase (NRPS) module and one polyketide synthase (PKS) module.[2][6][7][8] The single PKS module functions in a non-canonical fashion in that it is an iterative type I PKS responsible for the generation of the two unique polyketides needed in the backbone of HSAF using malonyl-CoA as both the starter and extender unit, while the NRPS module is responsible for the linking of the polyketides to an L-ornithine unit and the initial cyclization to create the tetramate back bone.[2][7][8]  The coding region related to HSAF production contains a PKS-NRPS with a total of 9 domains, (KS-AT-DH-KR-ACP-C-A-PCP-TE), while a cascade of FAD-dependent redox reactions (OX1-OX4) flank the PKS-NRPS cluster proposed to be responsible for formation of the 5,5,6-tricyclic system, there are additional coding regions for a putative regulator, an arginase for L-ornithine production from Arginine, and a transporter which flank the PKS-NRPS.[2][3][7][8]  Figure 1. Proposed mechanism of HSAF biosynthesis  Figure 2. Schematic of the function of the hybrid PKS-NRPS in the biosynthesis of HSAFReferences[edit]^ Graupner, P. R.; Thornburgh, S.; Mathieson, J. T.; Chapin, E. L.; Kemmitt, G. M.; Brown, J. M.; Snipes, C. E. (1997). “Dihydromaltophilin; a novel fungicidal tetramic acid containing metabolite from Streptomyces sp”. The Journal of Antibiotics. 50 (12): 1014\u20131019. doi:10.7164\/antibiotics.50.1014. ISSN\u00a00021-8820. PMID\u00a09510907.^ a b c d Xie, Yunxuan; Wright, Stephen; Shen, Yuemao; Du, Liangcheng (2012). “Bioactive natural products from Lysobacter”. Natural Product Reports. 29 (11): 1277\u20131287. doi:10.1039\/c2np20064c. ISSN\u00a01460-4752. PMC\u00a03468324. PMID\u00a022898908.^ a b Lou, Lili; Qian, Guoliang; Xie, Yunxuan; Hang, Jiliang; Chen, Haotong; Zaleta-Rivera, Kathia; Li, Yaoyao; Shen, Yuemao; Dussault, Patrick H. (2011-02-02). “Biosynthesis of HSAF, a tetramic acid-containing macrolactam from Lysobacter enzymogenes”. Journal of the American Chemical Society. 133 (4): 643\u2013645. doi:10.1021\/ja105732c. ISSN\u00a01520-5126. PMC\u00a03078565. PMID\u00a021171605.^ Li, Shaojie; Du, Liangcheng; Yuen, Gary; Harris, Steven D. (2006). “Distinct Ceramide Synthases Regulate Polarized Growth in the Filamentous Fungus Aspergillus nidulans”. Molecular Biology of the Cell. 17 (3): 1218\u20131227. doi:10.1091\/mbc.E05-06-0533. ISSN\u00a01059-1524. PMC\u00a01382311. PMID\u00a016394102.^ Li, Shaojie; Calvo, Ana M.; Yuen, Gary Y.; Du, Liangcheng; Harris, Steven D. (2009). “Induction of cell wall thickening by the antifungal compound dihydromaltophilin disrupts fungal growth and is mediated by sphingolipid biosynthesis”. The Journal of Eukaryotic Microbiology. 56 (2): 182\u2013187. doi:10.1111\/j.1550-7408.2008.00384.x. ISSN\u00a01550-7408. PMID\u00a021462551. S2CID\u00a033464609.^ Yu, Fengan; Zaleta-Rivera, Kathia; Zhu, Xiangcheng; Huffman, Justin; Millet, Jeffrey C.; Harris, Steven D.; Yuen, Gary; Li, Xing-Cong; Du, Liangcheng (2007-01-01). “Structure and Biosynthesis of Heat-Stable Antifungal Factor (HSAF), a Broad-Spectrum Antimycotic with a Novel Mode of Action”. Antimicrobial Agents and Chemotherapy. 51 (1): 64\u201372. doi:10.1128\/AAC.00931-06. ISSN\u00a00066-4804. PMC\u00a01797680. PMID\u00a017074795.^ a b c Li, Yaoyao; Chen, Haotong; Ding, Yanjiao; Xie, Yunxuan; Wang, Haoxin; Cerny, Ronald L.; Shen, Yuemao; Du, Liangcheng (2014-07-14). “Iterative assembly of two separate polyketide chains by the same single-module bacterial polyketide synthase in the biosynthesis of HSAF”. Angewandte Chemie International Edition. 53 (29): 7524\u20137530. doi:10.1002\/anie.201403500. ISSN\u00a01521-3773. PMC\u00a04107061. PMID\u00a024890524.^ a b c Chen, Haotong; Du, Liangcheng (2014). “Iterative polyketide biosynthesis by modular polyketide synthases in bacteria”. Applied Microbiology and Biotechnology. 100 (2): 541\u2013557. doi:10.1007\/s00253-015-7093-0. ISSN\u00a01432-0614. PMC\u00a04706475. PMID\u00a026549236.     (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4"},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki40\/dihydromaltophilin-wikipedia\/#breadcrumbitem","name":"Dihydromaltophilin – Wikipedia"}}]}]