[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki21\/aspergillomarasmine-a-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki21\/aspergillomarasmine-a-wikipedia\/","headline":"Aspergillomarasmine A – Wikipedia","name":"Aspergillomarasmine A – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia Aspergillomarasmine A Names IUPAC name (R-(R*,R*))-N-(2-((2-Amino-2-carboxyethyl)amino)-2-carboxyethyl)-L-aspartic acid[citation needed] Identifiers ChEMBL ChemSpider UNII after-content-x4 InChI=1S\/C10H17N3O8\/c11-4(8(16)17)2-12-6(10(20)21)3-13-5(9(18)19)1-7(14)15\/h4-6,12-13H,1-3,11H2,(H,14,15)(H,16,17)(H,18,19)(H,20,21)\/t4-,5+,6-\/m1\/s1","datePublished":"2017-06-16","dateModified":"2017-06-16","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki21\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki21\/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\/9\/9b\/Aspergillomarasmine_A.svg\/250px-Aspergillomarasmine_A.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/9\/9b\/Aspergillomarasmine_A.svg\/250px-Aspergillomarasmine_A.svg.png","height":"171","width":"250"},"url":"https:\/\/wiki.edu.vn\/en\/wiki21\/aspergillomarasmine-a-wikipedia\/","wordCount":3353,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopediaAspergillomarasmine ANamesIUPAC name(R-(R*,R*))-N-(2-((2-Amino-2-carboxyethyl)amino)-2-carboxyethyl)-L-aspartic acid[citation needed]IdentifiersChEMBLChemSpiderUNII       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4InChI=1S\/C10H17N3O8\/c11-4(8(16)17)2-12-6(10(20)21)3-13-5(9(18)19)1-7(14)15\/h4-6,12-13H,1-3,11H2,(H,14,15)(H,16,17)(H,18,19)(H,20,21)\/t4-,5+,6-\/m1\/s1       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Key:\u00a0XFTWUNOVBCHBJR-NGJCXOISSA-NC(C(C(=O)O)NCC(C(=O)O)NCC(C(=O)O)N)C(=O)OPropertiesC10H17N3O8Molar mass307.257Except where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compoundAspergillomarasmine A is an polyamino acid naturally produced by the mold Aspergillus versicolor. The substance has been reported to inhibit two antibiotic resistance carbapenemase proteins in bacteria, New Delhi metallo-beta-lactamase 1 (NDM-1) and Verona integron-encoded metallo-beta-lactamase (VIM-2), and make those antibiotic-resistant bacteria susceptible to antibiotics.[1] Aspergillomarasmine A is toxic to leaves of barley and other plants, being termed as “Toxin C” when produced by Pyrenophora teres.[2]       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4The molecule is a tetracarboxylic acid with four -COOH groups.  One section of the molecule is the amino acid aspartic acid. This has two alanine[contradictory] molecules attached by substituting a hydrogen on the methyl group with a link to the amine group. Aspergillomarasmine B differs in that the last alanine is replaced by glycine.The crystalline substance was first isolated in 1956, but its name was given until 1965.[3]In addition to Aspergillus versicolor, aspergillomarasmine A is also produced by the ascomycete Pyrenophora teres where it acts as a toxin in the barley net-spot blotch disease. In P. teres, a biosynthetic precursor of aspergillomarasmine A, L,L–N-(2-amino-2-carboxyethyl)-aspartic acid has also been isolated and found to contribute to the phytotoxic properties of this microbe.[4] This precursor, aspergillomarasmine A itself, and a lactam form (anhydroaspergillomarasmine A) are together termed the marasmines.[2]Other producers of aspergillomarasmine A include Aspergillus flavus,[3]Aspergillus oryzae,[5]Colletotrichum gloeosporioides, and Fusarium oxysporum.[2]In mice the LD50 toxic dose of aspergillomarasmine A is 159.8\u00a0mg\/kg.[6]Properties[edit]Aspergillomarasmine A takes the form of colourless crystals.  The chemical is insoluble in common organic solvents, but can dissolve in water under either basic or strongly acidic conditions.[3]Anhydroaspergillomarasmine A, a lactam of aspergillomarasmine A, chemically called [1-(2-amino-2carboxyethyl)-6-carboxy-3-carboxymethyl-3-piperazinone], can also be found in Pyrenophora teres. The relative amount of these two toxins is dependent upon the pH of the growth medium, with lower pH favouring the lactam form.[2]  The lactam can be hydrolyzed to aspergillomarasmine A by treating it with trifluoroacetic acid.[2]Aspergillomarasmine A functions as a chelating agent, sequestering Fe3+ ions.[7]  It can inhibit endothelin converting enzymes even in the live rat, probably by chelating metals required by metalloproteases.[8]When heated, aspergillomarasmine A decomposes between 225\u00b0 and 236\u00a0\u00b0C.  Hydrolysis produces L-aspartic acid and racemic[why?]2,3-diaminopropionic acid. Even though the precursor component is chiral, 2,3-diaminopropionic acid easily racemizes in acid.[3]Aspergillomarasmine A has [\u03b1]20\u00b0D at pH 7 of -48\u00b0.[3]With nitrous acid aspergillomarasmine A is deaminated,[clarification needed] and isoserine with aspartic acid is formed.[3]Titration reveals changes in ionisation at pK 3.5 and 4.5 due to carboxylic acid groups, and pK 9.5 and 10 due to amino groups.[3][clarification needed]Treatment with ninhydrin shows a purple colour.[3]References[edit]^ King, Andrew M.; Sarah A. Reid-Yu; Wenliang Wang; Dustin T. King; Gianfranco De Pascale; Natalie C. Strynadka; Timothy R. Walsh; Brian K. Coombes; Gerard D. Wright (2014). “Aspergillomarasmine A overcomes metallo-\u03b2-lactamase antibiotic resistance”. Nature. 510 (7506): 503\u2013506. Bibcode:2014Natur.510..503K. doi:10.1038\/nature13445. ISSN\u00a00028-0836. PMC\u00a04981499. PMID\u00a024965651.^ a b c d e Weiergang, I.; H.J. Lyngs J\u00f8rgensen; I.M. M\u00f8ller; P. Friis; V. Smedegaard-Petersen (2002). “Optimization of in vitro growth conditions of Pyrenophora teres for production of the phytotoxin aspergillomarasmine A”. Physiological and Molecular Plant Pathology. 60 (3): 131\u2013140. doi:10.1006\/pmpp.2002.0383. ISSN\u00a00885-5765.^ a b c d e f g h Haenni, A. L.; M. Robert; W. Vetter; L. Roux; M. Barbier; E. Lederer (1965). “Structure chimique des aspergillomarasmines A et B” [Chemical structure of aspergellomarasmines A and B]. Helvetica Chimica Acta (in French). 48 (4): 729\u2013750. doi:10.1002\/hlca.19650480409. ISSN\u00a00018-019X. PMID\u00a014321962.^ Friis, P; Olsen C.E.; M\u00f8ller B.L. (15 July 1991). “Toxin production in Pyrenophora teres, the ascomycete causing the net-spot blotch disease of barley (Hordeum vulgare L.)”. The Journal of Biological Chemistry. 266 (20): 13329\u201313335. doi:10.1016\/S0021-9258(18)98843-5. PMID\u00a02071605.^ Wagman, G.H.; Cooper, R. (1988-12-01). Natural Products Isolation: Separation Methods for Antimicrobials, Antivirals and Enzyme Inhibitors. Elsevier. p.\u00a0499. ISBN\u00a09780080858487. Retrieved 27 June 2014.^ Matsuura, Akihiro; Hiroshi Okumura; Rieko Asakura; Naoki Ashizawa; Mayumi Takahashi; Fujio Kobayashi; Nami Ashikawa; Koshi Arai (1993). “Pharmacological profiles of aspergillomarasmines as endothelin converting enzyme inhibitors”. The Japanese Journal of Pharmacology. 63 (2): 187\u2013193. doi:10.1254\/jjp.63.187. PMID\u00a08283829.^ Barbier, M. (1987). “Remarks on the biological activity of aspergillomarasmine A Fe3+ chelate and other iron transporting phytotoxins with reference to their role in the photodegradation of aromatic amino-acids in infected plant leaves”. Journal of Phytopathology. 120 (4): 365\u2013368. doi:10.1111\/j.1439-0434.1987.tb00500.x. ISSN\u00a00931-1785.^ Huggins, John P.; Pelton, John T. (1996-12-23). Endothelins in Biology and Medicine. CRC Press. p.\u00a0121. ISBN\u00a09780849369759. Retrieved 27 June 2014.       (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\/wiki21\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki21\/aspergillomarasmine-a-wikipedia\/#breadcrumbitem","name":"Aspergillomarasmine A – Wikipedia"}}]}]