| Identification | Back Directory | [Name]
THAXTOMINE A | [CAS]
122380-18-1 | [Synonyms]
MBI 005
THAXTOMINE A
Phytotoxin 1
Thaxtomin A, Cellulose synthesis inhibitor
(3R,6S)-3-Hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione
2,5-Piperazinedione, 3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-, (3R,6S)- | [Molecular Formula]
C22H22N4O6 | [MDL Number]
MFCD08457945 | [MOL File]
122380-18-1.mol | [Molecular Weight]
438.43 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMF: Soluble; DMSO: Soluble; Ethanol: Partially soluble; Methanol: Partially soluble | [form ]
powder | [color ]
yellow to orange | [InChIKey]
QRDNJYNIEGRRKV-XMSQKQJNSA-N | [SMILES]
O=C(N(C)[C@@H]1CC2=CNC3=C2C([N+]([O-])=O)=CC=C3)[C@@](CC4=CC(O)=CC=C4)(O)N(C)C1=O |
| Hazard Information | Back Directory | [Description]
Thaxtomin A is a major phytotoxin produced by S. scabies, gram-positive soil bacterium responsible for producing scabs on tubers and root vegetables. This bacterial metabolite acts as a virulence factor in the common scab potato disease and demonstrates herbicidal activity against the dicotyledon weeds B. campestris and A. retroflexus. | [Uses]
Thaxtomin A is a phytotoxin produced by Streptomyces scabies and other Streptomyces species, the causative agents of common scab disease in potato and other taproot crops. | [References]
[1] SYLVAIN LERAT. Involvement of the plant polymer Suberin and the disaccharide cellobiose in triggering thaxtomin A biosynthesis, a phytotoxin produced by the pathogenic agent streptomyces scabies.[J]. Phytopathology, 2010, 100 1: 91-96. DOI: 10.1094/phyto-100-1-0091
[2] HONGBO ZHANG. Total Synthesis of Thaxtomin A and Its Stereoisomers and Findings of Their Biological Activities[J]. Organic Letters, 2013, 15 22: 5670-5673. DOI: 10.1021/ol4026556 |
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Energy Chemical
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