A phytotoxin generated as a microbial metabolite
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Thaxtomin A

Item No. 15601

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione
CAS Number
122380-18-1
Molecular Formula
C22H22N4O6
Formula Weight
438.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: Partially solubleMethanol: Partially soluble
SMILES
O=C(N(C)[C@H]1CC2=CNC3=C2C([N+]([O-])=O)=CC=C3)[C@@](CC4=CC=CC(O)=C4)(O)N(C)C1=O
InChi Code
InChI=1S/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22+/m0/s1
InChi Key
QRDNJYNIEGRRKV-PGRDOPGGSA-N
Origin
Bacterium/Streptomyces bottropensis Gö-Dra 17
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Thaxtomin A is a major phytotoxin produced by S. scabies, gram-positive soil bacterium responsible for producing scabs on tubers and root vegetables.1 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.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lerat, S., Simao-Beaunoir, A.M., Wu, R., et al. Involvement of the plant polymer suberin and the disaccharide cellobiose in triggering thaxtomin A biosynthesis, a phytotoxin produced by the pathogenic agent Streptomyces scabies. Phytopathology 100(1), 91-96 (2010).

    2. Zhang, H., Ning, X., Hang, H., et al. Total synthesis of thaxtomin A and its stereoisomers and findings of their biological activities. Org. Lett. 15(22), 5670-5673 (2013).