Tagetitoxin

From Wikipedia, the free encyclopedia

Page Module:Message box/ambox.css has no content.

Page Template:Chembox/styles.css has no content.

Template:Chembox IndexlistTemplate:Chembox CompToxTemplate:Chembox Datapage check
Tagetitoxin
Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found.
Proposed structure of tagetitoxin
Identifiers
Page Template:Plainlist/styles.css has no content.
3D model (JSmol)
 Page Template:Plainlist/styles.css has no content.
ChemSpider Page Template:Plainlist/styles.css has no content.
EC Number Page Template:Plainlist/styles.css has no content.
Page Template:Plainlist/styles.css has no content.
RTECS number Page Template:Plainlist/styles.css has no content.
  • 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
    Key: UVAAUIDYGIWLMB-XJKNRETDSA-N
  • InChI=1/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
    Key: UVAAUIDYGIWLMB-XJKNRETDBI
  • O=C(N)[C@]1(O)SC[C@@]2(O[C@@H]1[C@H](OC(=O)C)[C@@H](N)[C@H]2OP(=O)(O)O)C(=O)O
Properties
C11H17N2O11PS
Molar mass 416.29 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Tagetitoxin (TGT) is a bacterial phytotoxin produced by Pseudomonas syringae pv. tagetis.[1][2]

Chemical structure

When TGT was first isolated, it was only partially characterized.[2] The first proposed chemical structure of TGT involved an eight-membered ring,[3] but this was revised shortly afterward to a bicyclic structure (shown at right) based on NMR and mass spectrometry.[4] This structure, however, has been questioned.[5] The absolute configuration remains undetermined, and attempts at confirming the structure by organic synthesis are underway.[6][7][8][9][10][11][12] In 2015, Porter et al. proposed an alternative structure of TGT based on extensive 2D NMR data.[13]

Mechanism of action

TGT interferes with development of chloroplasts in young plant leaves thereby causing chlorosis.[14] The natural target of the toxin is chloroplast RNA polymerase. Chloroplast RNA polymerase belongs to ubiquitous family of multisubunit RNA polymerases (RNAP) and is most closely related to bacterial enzymes. In vitro, TGT inhibits bacterial RNAPs from Escherichia coli and Thermus thermophilus, and eukaryotic RNA polymerase III.[15] In contrast, eukaryotic RNA polymerase I and II as well as single-subunit viral RNA polymerases are relatively insensitive to the compound. TGT binds in the bacterial enzyme's active site[16] and inhibits initiation and elongation phases of transcription as well as pyrophosphorolysis of the nascent RNA.[16] However, the detailed mechanism of inhibition remains a subject of heated debate.[17][18]

It has been suggested that TGT forms a ternary RNAP-NTP-TGT complex and inhibits phosphodiester bond synthesis either by binding an inhibitory magnesium ion[16] or by trapping a flexible active site domain in an inactive conformation.[19] The third theory suggests that TGT forms predominantly a binary RNAP-TGT complex and inhibits RNAP translocation along the DNA by mimicking the transcription byproduct pyrophosphate.[20]

References

Page Template:Reflist/styles.css has no content.

  1. ^ Page Module:Citation/CS1/styles.css has no content.Trimboli, D; Fahy, PC; Baker, KF (1978). "Apical chlorosis and leaf spot of Tagetes spp. Caused by Pseudomonas tagetis Hellmers". Australian Journal of Agricultural Research. 29 (4): 831–9. doi:10.1071/AR9780831.
  2. ^ a b Page Module:Citation/CS1/styles.css has no content.Mitchell, R. E.; Durbin, R. D. (1981). "Tagetitoxin, a toxin produced by Pseudomonas syringae pv. tagetis: purification and partial characterization". Physiological Plant Pathology. 18 (2): 157–68. doi:10.1016/S0048-4059(81)80037-9.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Mitchell, R. E.; Durbin, R. D. (1983). "The structure of tagetitoxin, a phytotoxin of Pseudomonas syringae pv. Tagetis". Phytochemistry. 22 (6): 1425–1428. Bibcode:1983PChem..22.1425M. doi:10.1016/S0031-9422(00)84028-5.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Mitchell, R. E.; Coddington, J. M.; Young, H. (1989). "A revised structure for tagetitoxin". Tetrahedron Lett. 30 (4): 501–504. doi:10.1016/S0040-4039(00)95239-0.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Gronwald, J.W.; Plaisance, K. L.; Marimanikkuppam, S.; Ostrowski, B. G. (2005). "Tagetitoxin purification and partial characterization". Physiol. Mol. Plant Pathol. 67 (1): 23–32. Bibcode:2005PMPP...67...23G. doi:10.1016/j.pmpp.2005.09.002.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Porter, Michael; Plet, Julien; Sandhu, Amandeep; Sehailia, Moussa (2009). "Thieme Chemistry Journal Awardees - Where Are They Now? Approaches to Tagetitoxin and its Decarboxy Analogue from d-Glucose". Synlett. 2009 (20): 3258–3262. doi:10.1055/s-0029-1218525.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Mortimer, Anne J. Price; Aliev, Abil E.; Tocher, Derek A.; Porter, Michael J. (2008). "Synthesis of the Tagetitoxin Core via Photo-Stevens Rearrangement". Organic Letters. 10 (23): 5477–80. doi:10.1021/ol802297h. PMID 18973329.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Sammakia, T.; Hurley, T. B.; Sammond, D. M.; Smith, R. S.; Sobolov, S. B.; Oeschger, T. R. (1996). "Dihydroxylation and oxidative cleavage of olefins in the presence of sulfur". Tetrahedron Lett. 37 (26): 4427–4430. doi:10.1016/0040-4039(96)00879-9.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Dent, B. R.; Furneaux, R. H.; Gainsford, G. J.; Lynch, G. P. (1999). "Synthesis studies of structural analogues of tagetitoxin: 2-phosphate". Tetrahedron. 55 (22): 6977–6996. doi:10.1016/S0040-4020(99)00327-0.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Plet, Julien R. H.; Porter, Michael J. (2006). "Synthesis of the bicyclic core of tagetitoxin". Chemical Communications. 44 (11): 1197–9. doi:10.1039/B600819D. PMID 16518489.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Mortimer, Anne J. P.; Plet, Julien R. H.; Obasanjo, Oluwafunsho A.; Kaltsoyannis, Nikolas; Porter, Michael J. (2012). "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. 10 (43): 8616–27. doi:10.1039/c2ob26308d. PMID 22965829. S2CID 43205302.,
  12. ^ Page Module:Citation/CS1/styles.css has no content.Sehailia, Moussa (2011). Studies towards the total synthesis of tagetitoxin (Doctoral thesis). University College London.[page needed]
  13. ^ Page Module:Citation/CS1/styles.css has no content.Aliev, Abil E.; Karu, Kersti; Mitchell, Robin E.; Porter, Michael J. (2015-12-15). "The structure of tagetitoxin" (PDF). Organic & Biomolecular Chemistry. 14 (1): 238–45. doi:10.1039/C5OB02076J. ISSN 1477-0539. PMID 26517805.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Lukens, J. H.; Durbin, R. D. (1985). "Tagetitoxin affects plastid development in seedling leaves of wheat". Planta. 165 (3): 311–21. Bibcode:1985Plant.165..311L. doi:10.1007/BF00392227. PMID 24241135. S2CID 40185810.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Steinberg, Thomas H.; Mathews, Dennis E.; Durbin, Richard D.; Burgess, Richard R. (1990). "Tagetitoxin: A New Inhibitor of Eukaryotic Transcription by RNA Polymerase III". The Journal of Biological Chemistry. 265 (1): 499–505. doi:10.1016/S0021-9258(19)40259-7. PMID 2403565.
  16. ^ a b c Page Module:Citation/CS1/styles.css has no content.Vassylyev, Dmitry G; Svetlov, Vladimir; Vassylyeva, Marina N; Perederina, Anna; Igarashi, Noriyuki; Matsugaki, Naohiro; Wakatsuki, Soichi; Artsimovitch, Irina (2005). "Structural basis for transcription inhibition by tagetitoxin". Nature Structural & Molecular Biology. 12 (12): 1086–93. doi:10.1038/nsmb1015. PMC 1790907. PMID 16273103.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Klyuyev, Sergiy; Vassylyev, Dmitry G. (2012). "The binding site and mechanism of the RNA polymerase inhibitor tagetitoxin: An issue open to debate". Transcription. 3 (2): 46–50. doi:10.4161/trns.19468. PMC 3337825. PMID 22414754.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Svetlov, Vladimir; Artsimovitch, Irina; Nudler, Evgeny (2012). "Response to Klyuyev and Vassylyev: On the mechanism of tagetitoxin inhibition of transcription". Transcription. 3 (2): 51–5. doi:10.4161/trns.19749. PMC 3337826. PMID 22414748.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Artsimovitch, Irina; Svetlov, Vladimir; Nemetski, Sondra Maureen; Epshtein, Vitaly; Cardozo, Timothy; Nudler, Evgeny (2011). "Tagetitoxin Inhibits RNA Polymerase through Trapping of the Trigger Loop". The Journal of Biological Chemistry. 286 (46): 40395–400. doi:10.1074/jbc.M111.300889. PMC 3220573. PMID 21976682.
  20. ^ Page Module:Citation/CS1/styles.css has no content.Malinen, Anssi M.; Turtola, Matti; Parthiban, Marimuthu; Vainonen, Lioudmila; Johnson, Mark S.; Belogurov, Georgiy A. (2012). "Active site opening and closure control translocation of multisubunit RNA polymerase". Nucleic Acids Research. 40 (15): 7442–51. doi:10.1093/nar/gks383. PMC 3424550. PMID 22570421.
Retrieved from "https://cosmopedia.co/index.php?title=Tagetitoxin&oldid=11453815"