Tagetitoxin | CAS#87913-21-1 | RNA synthesis inhibitor

MedKoo Cat#: 597304 | Name: Tagetitoxin

Description:

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

Tagetitoxin is a chlorosis-inducing phytoxin produced by Pseudomonas syringae pv. tagetis; inhibits RNA synthesis directed by chloroplast RNA polymerase.

Chemical Structure

Tagetitoxin

CAS#87913-21-1

Theoretical Analysis

MedKoo Cat#: 597304

Name: Tagetitoxin

CAS#: 87913-21-1

Chemical Formula: C11H17N2O11PS

Exact Mass: 416.0291

Molecular Weight: 416.29

Elemental Analysis: C, 31.74; H, 4.12; N, 6.73; O, 42.28; P, 7.44; S, 7.70

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

Tagetitoxin;

IUPAC/Chemical Name

(1S,4S,5S,6R,7R,8R)-6-acetoxy-7-amino-4-carbamoyl-4-hydroxy-8-(phosphonooxy)-9-oxa-3-thiabicyclo[3.3.1]nonane-1-carboxylic acid

InChi Key

UVAAUIDYGIWLMB-KCHUEWMZSA-N

InChi Code

InChI=1S/C11H17N2O11PS/c1-3(14)22-5-4(12)6(24-25(19,20)21)10(9(16)17)2-26-11(18,8(13)15)7(5)23-10/h4-7,18H,2,12H2,1H3,(H2,13,15)(H,16,17)(H2,19,20,21)/t4-,5-,6-,7+,10+,11+/m1/s1

SMILES Code

NC([C@@]1(O)SC[C@@]2(C(O)=O)[C@H](OP(O)(O)=O)[C@H](N)[C@@H](OC(C)=O)[C@@H]1O2)=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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 416.29 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.

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: Aliev AE, Karu K, Mitchell RE, Porter MJ. The structure of tagetitoxin. Org Biomol Chem. 2016 Jan 7;14(1):238-45. doi: 10.1039/c5ob02076j. Epub 2015 Oct 30. PubMed PMID: 26517805. 2: Yamada H, Adachi M, Nishikawa T. Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core structure of tagetitoxin. Chem Commun (Camb). 2013 Dec 11;49(95):11221-3. doi: 10.1039/c3cc46949b. Epub 2013 Oct 23. PubMed PMID: 24150697. 3: Yuzenkova Y, Roghanian M, Bochkareva A, Zenkin N. Tagetitoxin inhibits transcription by stabilizing pre-translocated state of the elongation complex. Nucleic Acids Res. 2013 Nov;41(20):9257-65. doi: 10.1093/nar/gkt708. Epub 2013 Aug 9. PubMed PMID: 23935117; PubMed Central PMCID: PMC3814378. 4: Nedialkov YA, Nudler E, Burton ZF. RNA polymerase stalls in a post-translocated register and can hyper-translocate. Transcription. 2012 Sep-Oct;3(5):260-9. doi: 10.4161/trns.22307. Epub 2012 Sep 1. PubMed PMID: 23132506; PubMed Central PMCID: PMC3632624. 5: Price Mortimer AJ, Plet JR, Obasanjo OA, Kaltsoyannis N, Porter MJ. Inter- and intramolecular reactions of 1-deoxy-1-thio-1,6-anhydrosugars with α-diazoesters: synthesis of the tagetitoxin core by photochemical ylide rearrangement. Org Biomol Chem. 2012 Nov 21;10(43):8616-27. doi: 10.1039/c2ob26308d. PubMed PMID: 22965829. 6: Malinen AM, Turtola M, Parthiban M, Vainonen L, Johnson MS, Belogurov GA. Active site opening and closure control translocation of multisubunit RNA polymerase. Nucleic Acids Res. 2012 Aug;40(15):7442-51. doi: 10.1093/nar/gks383. Epub 2012 May 8. PubMed PMID: 22570421; PubMed Central PMCID: PMC3424550. 7: Klyuyev S, Vassylyev DG. The binding site and mechanism of the RNA polymerase inhibitor tagetitoxin: an issue open to debate. Transcription. 2012 Mar-Apr;3(2):46-50. doi: 10.4161/trns.19468. Epub 2012 Mar 1. PubMed PMID: 22414754; PubMed Central PMCID: PMC3337825. 8: Svetlov V, Artsimovitch I, Nudler E. Response to Klyuyev and Vassylyev: on the mechanism of tagetitoxin inhibition of transcription. Transcription. 2012 Mar-Apr;3(2):51-5. doi: 10.4161/trns.19749. Epub 2012 Mar 1. PubMed PMID: 22414748; PubMed Central PMCID: PMC3337826. 9: Artsimovitch I, Svetlov V, Nemetski SM, Epshtein V, Cardozo T, Nudler E. Tagetitoxin inhibits RNA polymerase through trapping of the trigger loop. J Biol Chem. 2011 Nov 18;286(46):40395-400. doi: 10.1074/jbc.M111.300889. Epub 2011 Oct 5. PubMed PMID: 21976682; PubMed Central PMCID: PMC3220573. 10: Epshtein V, Dutta D, Wade J, Nudler E. An allosteric mechanism of Rho-dependent transcription termination. Nature. 2010 Jan 14;463(7278):245-9. doi: 10.1038/nature08669. Erratum in: Nature. 2010 Aug 19;466(7309):1006. PubMed PMID: 20075920; PubMed Central PMCID: PMC2929367. 11: Mortimer AJ, Aliev AE, Tocher DA, Porter MJ. Synthesis of the tagetitoxin core via photo-Stevens rearrangement. Org Lett. 2008 Dec 4;10(23):5477-80. doi: 10.1021/ol802297h. PubMed PMID: 18973329. 12: Kong H, Patterson CD, Mitchell RE, Buyer JS, Aime MC, Lydon J. A mutation in an exbD gene reduces tagetitoxin production by Pseudomonas syringae pv. tagetis. Can J Microbiol. 2006 Nov;52(11):1027-35. PubMed PMID: 17215893. 13: Zorov SD, Iuzenkova IuV, Severinov KV. [Low-molecular weight inhibitors of bacterial DNA-dependent RNA polymerase]. Mol Biol (Mosk). 2006 Nov-Dec;40(6):971-81. Review. Russian. PubMed PMID: 17209424. 14: Plet JR, Porter MJ. Synthesis of the bicyclic core of tagetitoxin. Chem Commun (Camb). 2006 Mar 21;(11):1197-9. Epub 2006 Feb 14. PubMed PMID: 16518489. 15: Vassylyev DG, Svetlov V, Vassylyeva MN, Perederina A, Igarashi N, Matsugaki N, Wakatsuki S, Artsimovitch I. Structural basis for transcription inhibition by tagetitoxin. Nat Struct Mol Biol. 2005 Dec;12(12):1086-93. Epub 2005 Nov 6. PubMed PMID: 16273103; PubMed Central PMCID: PMC1790907. 16: Witczak ZJ, Culhane JM. Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications. Appl Microbiol Biotechnol. 2005 Dec;69(3):237-44. Epub 2005 Nov 15. Review. PubMed PMID: 16240117. 17: Kabeya Y, Sato N. Unique translation initiation at the second AUG codon determines mitochondrial localization of the phage-type RNA polymerases in the moss Physcomitrella patens. Plant Physiol. 2005 May;138(1):369-82. Epub 2005 Apr 15. PubMed PMID: 15834007; PubMed Central PMCID: PMC1104190. 18: Martínez-Calvillo S, Nguyen D, Stuart K, Myler PJ. Transcription initiation and termination on Leishmania major chromosome 3. Eukaryot Cell. 2004 Apr;3(2):506-17. PubMed PMID: 15075279; PubMed Central PMCID: PMC387636. 19: Lilly JW, Maul JE, Stern DB. The Chlamydomonas reinhardtii organellar genomes respond transcriptionally and post-transcriptionally to abiotic stimuli. Plant Cell. 2002 Nov;14(11):2681-706. Retraction in: Plant Cell. 2004 Mar;16(3):785. PubMed PMID: 12417695; PubMed Central PMCID: PMC152721. 20: Ioannou M, Porter MJ, Saez F. A ring expansion reaction of 1,3-oxathiolanes. Chem Commun (Camb). 2002 Feb 21;(4):346-7. PubMed PMID: 12120067.