Overview

  • Product name

    Thaxtomin A, Cellulose synthesis inhibitor
  • Description

    Phytotoxin. Potent necrotic agent. Cellulose synthesis inhibitor.
  • Biological description

    Phytotoxin and potent necrotic agent. Cellulose synthesis inhibitor. Bacterial NOS metabolite. Inhibits cellulose synthesis in expanding plant tissues. Herbicidal effects in vivo.
  • Purity

    > 98%
  • CAS Number

    122380-18-1
  • Chemical structure

    Chemical Structure

Properties

  • Chemical name

    (3R,6S)-3-Hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione
  • Molecular weight

    438.43
  • Molecular formula

    C22H22N4O6
  • PubChem identifier

    180098
  • Storage instructions

    Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.
  • Solubility overview

    Soluble in ethanol and in DMSO
  • Handling

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

  • SMILES

    CN1[C@H](C(=O)N([C@](C1=O)(CC2=CC(=CC=C2)O)O)C)CC3=CNC4=C3C(=CC=C4)[N+](=O)[O-]
  • Source

    Streptomyces bottropensis

  • Research areas

References

This product has been referenced in:

  • Brochu V  et al. Habituation to thaxtomin A in hybrid poplar cell suspensions provides enhanced and durable resistance to inhibitors of cellulose synthesis. BMC Plant Biol 10:272 (2010). Read more (PubMed: 21143977) »
  • Bischoff V  et al. Thaxtomin A affects CESA-complex density, expression of cell wall genes, cell wall composition, and causes ectopic lignification in Arabidopsis thaliana seedlings. J Exp Bot 60:955-65 (2009). Read more (PubMed: 19269997) »
  • Loria R  et al. Thaxtomin biosynthesis: the path to plant pathogenicity in the genus Streptomyces. Antonie Van Leeuwenhoek 94:3-10 (2008). Read more (PubMed: 18392685) »

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