BioViotica

Thaxtomin A

CHF 215.00
In stock
BVT-0206-M0011 mgCHF 215.00
BVT-0206-M0055 mgCHF 755.00
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Product Details
Synonyms Thaztomin A
Product Type Chemical
Properties
Formula

C22H22N4O6

MW 438.4
CAS 122380-18-1
Source/Host Chemicals Isolated from Streptomyces bottropensis Gö-Dra 17.
Purity Chemicals ≥98% (HPLC)
Appearance Yellow powder.
Solubility Soluble in DMSO or dimethyl formamide; partially soluble in methanol or 100% ethanol; poorly soluble in water.
Identity Determined by 1H-NMR.
Declaration Manufactured by BioViotica.
InChi Key QRDNJYNIEGRRKV-PGRDOPGGSA-N
Smiles CN1[C@@H](CC2=CNC3=C2C(=CC=C3)[N+]([O-])=O)C(=O)N(C)[C@@](O)(CC2=CC(O)=CC=C2)C1=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Use/Stability Stable for at least 1 year after receipt when stored at -20°C.
After reconstitution protect from light at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Diketopiperazine antibiotic.
  • Phytotoxin.
  • Herbicide.
  • Natural cellulose synthesis inhibitor.
  • Plant cell necrosis inducer.
  • Induces common scab disease of potato.
Product References
  1. Isolation and characterization of phytotoxins associated with Streptomyces scabies: R. R. King, et al.; J. Chem. Soc. Chem. Commun. 13, 849 (1989)
  2. An Arabidopsis mutant resistant to thaxtomin A, a cellulose synthesis inhibitor from Streptomyces species: W.R. Scheible, et al.; Plant Cell 15, 1781 (2003)
  3. Thaxtomin A induces programmed cell death in Arabidopsis thaliana suspension-cultured cells: I. Duval, et al.; Planta 222, 820 (2005)
  4. The Thaxtomin phytotoxins: Sources, synthesis, biosynthesis, biotransformation and biological activity: R. R. King & L. A. Calhoun; Phytochemistry 70, 833 (2009) (Review)
  5. Streptomyces scabiei and its toxin thaxtomin A induce scopoletin biosynthesis in tobacco and Arabidopsis thaliana: S. Lerat, et. al.; Plant Cell Rep. 28, 1895 (2009)
  6. Two different signaling pathways for Thaxtomin A-induced cell death in Arabidopsis and tobacco BY2: P. Meimoun, et al.; Plant Sign. Behav. 4, 142 (2009)
  7. Relationship of resistance to common scab disease and tolerance to thaxtomin A toxicity within potato cultivars: R. S. Tegg, et al.; Eur. J. Plant Pathol. 128, 143 (2010)
  8. Total synthesis of thaxtomin A and its stereoisomers and findings of their biological activities: H. Zhang, et al.; Org. Lett. 15, 5670 (2013)
  9. Thaxtomin A production and virulence are controlled by several bld gene global regulators in Streptomyces scabies: D. Bignell, et al.; Mol. Plant Microbe Interact. 27, 875 (2014)
  10. Mechanisms of thaxtomin A-induced root toxicity revealed by a thaxtomin A sensitive Arabidopsis mutant (ucu2-2/gi-2): R.S. Tegg, et al.; Plant Cell Rep. 35, 347 (2016)
  11. De novo biosynthesis of "non-natural" thaxtomin phytotoxins: M. Winn, et al.; Angew. Chem. Int. Ed. 57, 6830 (2018)
  12. Evaluation of Streptomyces common scab toxins diffusion in potato tubers and through the intestinal barrier: C. Leclerc, et al.; Int. J. Curr. Microbiol. Appl. Sci. 6, 1662 (2017)
  13. The emergence of nitric oxide in the biosynthesis of bacterial natural products: J D. Caranto; Curr. Opin. Chem. Biol. 49, 130 (2019)
  14. Chemical activation of EDS1/PAD4 signaling leading to pathogen resistance in Arabidopsis: S. Joglekar, et al.; Plant Cell Physiol. 59, 1592 (2018)
  15. Reactive oxygen species alleviate cell death induced by thaxtomin A in Arabidopsis thaliana cell cultures: F. Awwad, et al.; Plants 8, 332 (2019)
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