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rac-GR24 CAS: 76974-79-3

Category: Reference-Standards
Product Name: rac-GR24
Cat No: R034890
CAS No: 76974-79-3
Synonyms: [3E(R*),3aα,8bα]-(±)-3-[[(2,5-Dihydro-4-methyl-5-oxo-2-furanyl)oxy]methylene]-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one; rel-(3E,3aR,8bS)-3-[[[(2R)-2,5-Dihydro-4-methyl-5-oxo-2-furanyl]oxy]methylene]-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one
Molecular Formula: C17H14O5
Molecular Weight: 298.29
Inventory Status: In Stock > 5g;
CAS 76974-79-3,rac-GR24
  • Description

rac-GR24(cas 76974-79-3) is a potent synthetic strigolactone analog.

 Treatment of Gigaspora rosea with a strigolactone analog (GR24) causes a rapid increase in the NADH concentration, the NADH dehydrogenase activity, and the ATP content of the fungal cell. This fully and rapidly (within minutes) activated oxidative metabolism does not require new gene expression. Up-regulation of the genes involved in mitochondrial metabolism and hyphal growth, and stimulation of the fungal mitotic activity.

  • Spec

Purity: > 98%

  • References

1: Li S, Chen L, Li Y, Yao R, Wang F, Yang M, Gu M, Nan F, Xie D, Yan J. Effect of GR24 Stereoisomers on Plant Development in Arabidopsis. Mol Plant. 2016 Oct 10;9(10):1432-1435. doi: 10.1016/j.molp.2016.06.012. Epub 2016 Jul 1. PubMed PMID: 27378724.
2: Walton A, Stes E, Goeminne G, Braem L, Vuylsteke M, Matthys C, De Cuyper C, Staes A, Vandenbussche J, Boyer FD, Vanholme R, Fromentin J, Boerjan W, Gevaert K, Goormachtig S. The Response of the Root Proteome to the Synthetic Strigolactone GR24 in Arabidopsis. Mol Cell Proteomics. 2016 Aug;15(8):2744-55. doi: 10.1074/mcp.M115.050062. Epub 2016 Jun 17. PubMed PMID: 27317401; PubMed Central PMCID: PMC4974348.
3: Morris JC, McErlean CS. Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24. Org Biomol Chem. 2016 Jan 28;14(4):1236-8. doi: 10.1039/c5ob02349a. Epub 2015 Dec 21. PubMed PMID: 26691225.
4: Ueno K, Ishiwa S, Nakashima H, Mizutani M, Takikawa H, Sugimoto Y. Regioselective and stereospecific hydroxylation of GR24 by Sorghum bicolor and evaluation of germination inducing activities of hydroxylated GR24 stereoisomers toward seeds of Striga species. Bioorg Med Chem. 2015 Sep 15;23(18):6100-10. doi: 10.1016/j.bmc.2015.08.003. Epub 2015 Aug 12. PubMed PMID: 26320663.
5: De Cuyper C, Fromentin J, Yocgo RE, De Keyser A, Guillotin B, Kunert K, Boyer FD, Goormachtig S. From lateral root density to nodule number, the strigolactone analogue GR24 shapes the root architecture of Medicago truncatula. J Exp Bot. 2015 Jul;66(13):4091. doi: 10.1093/jxb/erv227. Epub 2015 Jun 4. PubMed PMID: 26044093.
6: De Cuyper C, Fromentin J, Yocgo RE, De Keyser A, Guillotin B, Kunert K, Boyer FD, Goormachtig S. From lateral root density to nodule number, the strigolactone analogue GR24 shapes the root architecture of Medicago truncatula. J Exp Bot. 2015 Jan;66(1):137-46. doi: 10.1093/jxb/eru404. Epub 2014 Nov 4. Erratum in: J Exp Bot. 2015 Jul;66(13):4091. PubMed PMID: 25371499.
7: Pandya-Kumar N, Shema R, Kumar M, Mayzlish-Gati E, Levy D, Zemach H, Belausov E, Wininger S, Abu-Abied M, Kapulnik Y, Koltai H. Strigolactone analog GR24 triggers changes in PIN2 polarity, vesicle trafficking and actin filament architecture. New Phytol. 2014 Jun;202(4):1184-96. doi: 10.1111/nph.12744. Epub 2014 Feb 25. PubMed PMID: 24571327.
8: Bromhead LJ, Visser J, McErlean CS. Enantioselective synthesis of the strigolactone mimic (+)-GR24. J Org Chem. 2014 Feb 7;79(3):1516-20. doi: 10.1021/jo402722p. Epub 2014 Jan 17. PubMed PMID: 24422520.
9: Islam S, Griffiths CA, Blomstedt CK, Le TN, Gaff DF, Hamill JD, Neale AD. Increased biomass, seed yield and stress tolerance is conferred in Arabidopsis by a novel enzyme from the resurrection grass Sporobolus stapfianus that glycosylates the strigolactone analogue GR24. PLoS One. 2013 Nov 5;8(11):e80035. doi: 10.1371/journal.pone.0080035. eCollection 2013. PubMed PMID: 24224034; PubMed Central PMCID: PMC3818285.
10: Rasmussen A, Heugebaert T, Matthys C, Van Deun R, Boyer FD, Goormachtig S, Stevens C, Geelen D. A fluorescent alternative to the synthetic strigolactone GR24. Mol Plant. 2013 Jan;6(1):100-12. doi: 10.1093/mp/sss110. Epub 2012 Sep 30. PubMed PMID: 23024210.
11: Lechat MM, Pouvreau JB, Péron T, Gauthier M, Montiel G, Véronési C, Todoroki Y, Le Bizec B, Monteau F, Macherel D, Simier P, Thoiron S, Delavault P. PrCYP707A1, an ABA catabolic gene, is a key component of Phelipanche ramosa seed germination in response to the strigolactone analogue GR24. J Exp Bot. 2012 Sep;63(14):5311-22. doi: 10.1093/jxb/ers189. Epub 2012 Aug 1. PubMed PMID: 22859674; PubMed Central PMCID: PMC3431000.
12: Dor E, Joel DM, Kapulnik Y, Koltai H, Hershenhorn J. The synthetic strigolactone GR24 influences the growth pattern of phytopathogenic fungi. Planta. 2011 Aug;234(2):419-27. doi: 10.1007/s00425-011-1452-6. Epub 2011 Jun 19. PubMed PMID: 21688170.
13: Ruyter-Spira C, Kohlen W, Charnikhova T, van Zeijl A, van Bezouwen L, de Ruijter N, Cardoso C, Lopez-Raez JA, Matusova R, Bours R, Verstappen F, Bouwmeester H. Physiological effects of the synthetic strigolactone analog GR24 on root system architecture in Arabidopsis: another belowground role for strigolactones? Plant Physiol. 2011 Feb;155(2):721-34. doi: 10.1104/pp.110.166645. Epub 2010 Nov 30. PubMed PMID: 21119044; PubMed Central PMCID: PMC3032462.
14: Besserer A, Bécard G, Jauneau A, Roux C, Séjalon-Delmas N. GR24, a synthetic analog of strigolactones, stimulates the mitosis and growth of the arbuscular mycorrhizal fungus Gigaspora rosea by boosting its energy metabolism. Plant Physiol. 2008 Sep;148(1):402-13. doi: 10.1104/pp.108.121400. Epub 2008 Jul 9. PubMed PMID: 18614712; PubMed Central PMCID: PMC2528133.

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