Aspergillomarasmine A
250px | |
Names | |
---|---|
IUPAC name
(R-(R*,R*))-N-(2-((2-Amino-2-carboxyethyl)amino)-2-carboxyethyl)-L-aspartic acid[citation needed]
|
|
Identifiers | |
3484-65-9 | |
ChemSpider | 170641 |
Jmol 3D model | Interactive image |
PubChem | 197028 |
|
|
|
|
Properties | |
C10H17N3O8 | |
Molar mass | 307.257 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
Infobox references | |
Aspergillomarasmine 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]
The 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. 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 mg/kg.[6]
Properties
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° and 236 °C. Hydrolysis produces L-aspartic acid and racemic[why?] 2,3-diamino-propionic acid. [α]20°D at pH 7 is -48°.[3][contradictory]
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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 2.0 2.1 2.2 2.3 2.4 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- Pages with broken file links
- Articles with unsourced statements from February 2016
- Articles without EBI source
- Articles without KEGG source
- Articles without UNII source
- Pages using collapsible list with both background and text-align in titlestyle
- Chemical articles using a fixed chemical formula
- Articles containing unverified chemical infoboxes
- Wikipedia articles needing clarification from February 2016
- Antibiotic resistance