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MedKoo Cat#: 562610 | Name: Thaxtomin A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thaxtomin A is a phytotoxin that causes plant cell necrosis.

Chemical Structure

Thaxtomin A
Thaxtomin A
CAS#122380-18-1

Theoretical Analysis

MedKoo Cat#: 562610

Name: Thaxtomin A

CAS#: 122380-18-1

Chemical Formula: C22H22N4O6

Exact Mass: 438.1539

Molecular Weight: 438.44

Elemental Analysis: C, 60.27; H, 5.06; N, 12.78; O, 21.89

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Thaxtomin A; Thaxtomin-A; ThaxtominA; Thaxtomine A; Thaxtomine-A; Phytotoxin 1; Phytotoxin-1; NSC630669; NSC-630669; NSC 630669;
IUPAC/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
InChi Key
QRDNJYNIEGRRKV-PGRDOPGGSA-N
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
SMILES Code
O=C([C@@](CC1=CC=CC(O)=C1)(O)N2C)N(C)[C@@H](CC3=CNC4=C3C([N+]([O-])=O)=CC=C4)C2=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 438.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jiang G, Zhang Y, Powell MM, Zhang P, Zuo R, Zhang Y, Kallifidas D, Tieu AM, Luesch H, Loria R, Ding Y. High-yield production of herbicidal thaxtomins and analogs in a nonpathogenic Streptomyces strain. Appl Environ Microbiol. 2018 Mar 30. pii: AEM.00164-18. doi: 10.1128/AEM.00164-18. [Epub ahead of print] PubMed PMID: 29602787. 2: Zhang Y, Jiang G, Ding Y, Loria R. Genetic background affects pathogenicity island function and pathogen emergence in Streptomyces. Mol Plant Pathol. 2018 Jan 9. doi: 10.1111/mpp.12656. [Epub ahead of print] PubMed PMID: 29316196. 3: Jourdan S, Francis IM, Deflandre B, Tenconi E, Riley J, Planckaert S, Tocquin P, Martinet L, Devreese B, Loria R, Rigali S. Contribution of the β-glucosidase BglC to the onset of the pathogenic lifestyle of Streptomyces scabies. Mol Plant Pathol. 2018 Jun;19(6):1480-1490. doi: 10.1111/mpp.12631. Epub 2017 Dec 26. PubMed PMID: 29077242. 4: Bown L, Bignell DRD. Draft Genome Sequence of the Plant Pathogen Streptomyces sp. Strain 11-1-2. Genome Announc. 2017 Sep 14;5(37). pii: e00968-17. doi: 10.1128/genomeA.00968-17. PubMed PMID: 28912321; PubMed Central PMCID: PMC5597762. 5: Zhang Y, Loria R. Emergence of Novel Pathogenic Streptomyces Species by Site-Specific Accretion and cis-Mobilization of Pathogenicity Islands. Mol Plant Microbe Interact. 2017 Jan;30(1):72-82. doi: 10.1094/MPMI-09-16-0190-R. Epub 2017 Jan 30. PubMed PMID: 27977935. 6: Zhang Y, Bignell DR, Zuo R, Fan Q, Huguet-Tapia JC, Ding Y, Loria R. Promiscuous Pathogenicity Islands and Phylogeny of Pathogenic Streptomyces spp. Mol Plant Microbe Interact. 2016 Aug;29(8):640-50. doi: 10.1094/MPMI-04-16-0068-R. Epub 2016 Aug 9. PubMed PMID: 27502745. 7: Jourdan S, Francis IM, Kim MJ, Salazar JJ, Planckaert S, Frère JM, Matagne A, Kerff F, Devreese B, Loria R, Rigali S. The CebE/MsiK Transporter is a Doorway to the Cello-oligosaccharide-mediated Induction of Streptomyces scabies Pathogenicity. Sci Rep. 2016 Jun 2;6:27144. doi: 10.1038/srep27144. PubMed PMID: 27250236; PubMed Central PMCID: PMC4890002. 8: Thangavel T, Tegg RS, Wilson CR. Toughing It Out--Disease-Resistant Potato Mutants Have Enhanced Tuber Skin Defenses. Phytopathology. 2016 May;106(5):474-83. doi: 10.1094/PHYTO-08-15-0191-R. Epub 2016 Mar 21. PubMed PMID: 26780437. 9: Fyans JK, Bown L, Bignell DR. Isolation and Characterization of Plant-Pathogenic Streptomyces Species Associated with Common Scab-Infected Potato Tubers in Newfoundland. Phytopathology. 2016 Feb;106(2):123-31. doi: 10.1094/PHYTO-05-15-0125-R. Epub 2016 Jan 29. PubMed PMID: 26524546. 10: Tegg RS, Shabala S, Cuin TA, Wilson CR. Mechanisms of thaxtomin A-induced root toxicity revealed by a thaxtomin A sensitive Arabidopsis mutant (ucu2-2/gi-2). Plant Cell Rep. 2016 Feb;35(2):347-56. doi: 10.1007/s00299-015-1888-4. Epub 2015 Oct 30. PubMed PMID: 26518425. 11: Arseneault T, Goyer C, Filion M. Pseudomonas fluorescens LBUM223 Increases Potato Yield and Reduces Common Scab Symptoms in the Field. Phytopathology. 2015 Oct;105(10):1311-7. doi: 10.1094/PHYTO-12-14-0358-R. Epub 2015 Sep 11. PubMed PMID: 25961336. 12: Cheng Z, Bown L, Tahlan K, Bignell DR. Regulation of coronafacoyl phytotoxin production by the PAS-LuxR family regulator CfaR in the common scab pathogen Streptomyces scabies. PLoS One. 2015 Mar 31;10(3):e0122450. doi: 10.1371/journal.pone.0122450. eCollection 2015. PubMed PMID: 25826255; PubMed Central PMCID: PMC4380410. 13: Park JM, Choi SU. Identification of a novel unpaired histidine sensor kinase affecting secondary metabolism and morphological differentiation in Streptomyces acidiscabies ATCC 49003. Folia Microbiol (Praha). 2015 Jul;60(4):279-87. doi: 10.1007/s12223-015-0383-1. Epub 2015 Mar 29. PubMed PMID: 25821125. 14: Zhang H, Wang Q, Ning X, Hang H, Ma J, Yang X, Lu X, Zhang J, Li Y, Niu C, Song H, Wang X, Wang PG. Synthesis and biological evaluations of a series of thaxtomin analogues. J Agric Food Chem. 2015 Apr 15;63(14):3734-41. doi: 10.1021/jf506153t. Epub 2015 Apr 3. PubMed PMID: 25804187. 15: Francis IM, Jourdan S, Fanara S, Loria R, Rigali S. The cellobiose sensor CebR is the gatekeeper of Streptomyces scabies pathogenicity. MBio. 2015 Feb 24;6(2):e02018. doi: 10.1128/mBio.02018-14. PubMed PMID: 25714708; PubMed Central PMCID: PMC4358012. 16: Fyans JK, Altowairish MS, Li Y, Bignell DR. Characterization of the Coronatine-Like Phytotoxins Produced by the Common Scab Pathogen Streptomyces scabies. Mol Plant Microbe Interact. 2015 Apr;28(4):443-54. doi: 10.1094/MPMI-09-14-0255-R. PubMed PMID: 25423263. 17: Bourgault JP, Maddirala AR, Andreana PR. A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A. Org Biomol Chem. 2014 Nov 7;12(41):8125-7. doi: 10.1039/c4ob01148a. Epub 2014 Jul 24. PubMed PMID: 25058709. 18: Bignell DR, Francis IM, Fyans JK, Loria R. Thaxtomin A production and virulence are controlled by several bld gene global regulators in Streptomyces scabies. Mol Plant Microbe Interact. 2014 Aug;27(8):875-85. doi: 10.1094/MPMI-02-14-0037-R. PubMed PMID: 24678834. 19: Yu F, Li M, Xu C, Wang Z, Zhou H, Yang M, Chen Y, Tang L, He J. Structural insights into the mechanism for recognizing substrate of the cytochrome P450 enzyme TxtE. PLoS One. 2013 Nov 25;8(11):e81526. doi: 10.1371/journal.pone.0081526. eCollection 2013. PubMed PMID: 24282603; PubMed Central PMCID: PMC3840065. 20: Zhang H, Ning X, Hang H, Ru X, Li H, Li Y, Wang L, Zhang X, Yu S, Qiao Y, Wang X, Wang PG. Total synthesis of thaxtomin A and its stereoisomers and findings of their biological activities. Org Lett. 2013 Nov 15;15(22):5670-3. doi: 10.1021/ol4026556. Epub 2013 Oct 25. PubMed PMID: 24159901.

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