An efficient microwave-assisted enzyme-catalyzed regioselective synthesis of long chain acylated derivatives of flavonoid glycosides

Tetrahedron Letters

Volumn 54, Issue 15, 2013, Pages 1933-1937

  Ziaullah, ^a   Rupasinghe, H P Vasantha ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

13C NMR spectroscopy; 1H NMR; Acylation; Candida antartica lipase B; Isoquercitrin; Microwave irradiation; Phloridzin

Indexed keywords

FLAVONOID GLYCOSIDE; ISOQUERCITRIN; PHLORIZIN; POLYUNSATURATED FATTY ACID; SATURATED FATTY ACID;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENZYME SYNTHESIS; MICROWAVE IRRADIATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

CANDIDA;

EID: 84874945816     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.103     Document Type: Article

References (63)

1. Kappe, C. O.; Dallinger, D. Mol. Diversity 2009, 13, 71.
2. Loupy, A. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2006.
3. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
4. Kappe, C. O. Microwaves in Organic and Medicinal Chemistry. Wiley-VCH: Weinheim, Germany, 2005.
5. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
6. Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light. CEM Publishing: Matthews, NC, 2003.
7. Mingos, D. M. P.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
8. Herrero, M. A.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 36.
9. Hayes, B. L. Aldrichim. Acta 2004, 37, 66.
10. Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141.
11. Rejasse, B.; Lamare, S.; Legoy, M. D.; Besson, T. J. Enzyme Inhib. 2007, 22, 518.
12. Rejasse, B.; Lamare, S.; Legoy, M. D.; Besson, T. J. Enzyme Inhib. Med. Chem. 2007, 22, 518.
13. Parker, M. C.; Besson, T.; Lamare, S.; Legoy, M. D. Tetrahedron Lett. 1996, 37, 8383.
14. Yadav, G. D.; Lathi, P. Synth. Commun. 2005, 35, 1699.
15. Yadav, G. D.; Sajgure, A. D.; Dhoot, S. B. In Enzyme Mixtures and Complex Biosynthesis. Bhattacharya, S. K., Ed.; Landes Biosciences: Austin, TX, 2007.
16. Austin, Y. D.; Tian, L.; Ma, D.; Wu, H.; Wang, Z.; Wang, L.; Fang, X. Green Chem. 2010, 12, 844.
17. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
18. Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406.
19. Elander, N.; Jones, J. R.; Lu, S. Y.; Stone-Elander, S. Chem. Soc. Rev. 2000, 29, 239.
20. Suarez, M.; Loupy, A.; Salfran, E.; Moran, L.; Rolando, E. Heterocycles 1999, 51, 21.
21. Loupy, A.; Regnier, S. Tetrahedron Lett. 1999, 40, 6221.
22. Olofsson, K.; Kim, S. Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539.
23. Orru, R. V. A.; de Greef, M. Synth. Stuttg. 2003, 1471.
24. Nuchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 6, 128.
25. Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S. J.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213.
26. Gedye, R. N.; Wei, J. B. Can. J. Chem. 1998, 76, 525.
27. Langa, F.; DelaCruz, P.; DelaHoz, A.; DiazOrtiz, A.; DiezBarra, E. Contemp. Org. Synth. 1997, 4, 373.
28. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synth. Stuttg. 1998, 1213.
29. Chen, S.-T.; Chiou, S.-H.; Wang, K.-T. J. Chin. Chem. Soc. 1991, 38, 85.
30. Bose, A. K.; Ing, Y. H.; Lavlinskaia, N.; Sareen, C.; Pramanik, B. N.; Bartner, P. L.; Liu, Y. H.; Heimark, L. J. Am. Soc. Mass Spectrom. 2002, 13, 839.
31. Pramanik, B. N.; Mirza, U. A.; Ing, Y. H.; Liu, Y. H.; Bartner, P. L.; Weber, P. C.; Bose, M. K. Protein Sci. 2002, 11, 2676.
32. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Free Radical Biol. Med. 1996, 20, 933.
33. Thilakarathna, S. H.; Rupasinghe, H. P. V. Can. J. Plant Sci. 2012, 92, 407.
34. Balasuriya, N.; Rupasinghe, H. P. V. Food Chem. 2012, 135, 2320.
35. Formica, J. V.; Regelson, W. Food Chem. Toxicol. 1995, 33, 1061.
36. Harborne, J. B.; Williams, C. A. Phytochemistry 2000, 55, 481.
37. Hossion, A. M. L.; Otsuka, N.; Kandahary, R. K.; Tsuchiya, T.; Ogawa, W.; Iwado, A.; Zamami, Y.; Sasaki, K. Bioorg. Med. Chem. Lett. 2010, 20, 5349.
38. Lee, K. Med. Res. Rev. 1999, 19, 569.
39. Tijburg, L. B. M.; Mattern, T.; Folts, J. D.; Weisgerber, U. M.; Katan, M. B. Crit. Rev. Food Sci. Nutr. 1997, 37, 771.
40. Mellou, F.; Loutrari, H.; Stamatis, H.; Roussos, C.; Kolisis, F. N. Process Biochem. 2006, 41, 2029.
41. Hilt, P.; Schieber, A.; Yildrim, C.; Arnold, G.; Klaiber, I.; Conrad, J.; Beifuss, U.; Carle, R. J. Agric. Food Chem. 2003, 51, 2896.
42. Salem, J. H.; Humeau, C.; Chevalot, I.; Harscoat-Schiavo, C.; Vanderesse, R.; Blanchard, F.; Fick, M. Process Biochem. 2010, 45, 382.
43. Aursand, M.; Grasdalen, H. Chem. Phys. Lipids 1992, 62, 239.
44. Stevenson, D. E.; Wibisono, R.; Jensen, D. J.; Stanley, R. A.; Cooney, J. M. Enzyme Microb. Technol. 2006, 39, 1236.
45. Ardhaoui, M.; Falcimaigne, A.; Ognier, S.; Engasser, J. M.; Moussou, P.; Pauly, G.; Ghoul, M. J. Biotechnol. 2004, 110, 265.
46. Lue, B.-M.; Guo, Z.; Xu, X. Process Biochem. 2010, 45, 1375.
47. Gao, C.; Mayon, P.; MacManus, D. A.; Vulfson, E. N. Biotechnol. Bioeng. 2000-2001, 71, 235.
48. Kontogianni, A.; Skouridou, V.; Sereti, V.; Stamatis, H.; Kolisis, F. N. Eur. J. Lipid Sci. Technol. 2001, 103, 655.
49. Mellou, F.; Lazari, D.; Skaltsa, H.; Tselepis, A. D.; Kolisis, F. N.; Stamatis, H. J. Biotechnol. 2005, 116, 295.
50. Yang, Z.; Pan, W. Enzyme Microb. Technol. 2005, 37, 19.
51. Rantwijk, F. V.; Sheldon, R. A. Chem. Rev. 2007, 107, 2757.
52. Kidwai, M.; Poddar, R. Catal. Lett. 2008, 124, 311.
53. Réjasse, B.; BessonEn, T.; Legoy, M.-D.; Lamare, S. Org. Biomol. Chem. 2006, 4, 3703.
54. Hilt, P.; Schieber, A.; Yildrim, C.; Arnold, G.; Klaiber, I.; Conrad, J.; Beifuss, U.; Carle, R. J. Agric. Food Chem. 2003, 51, 2896.
55. Salem, J. H.; Humeau, C.; Chevalot, I.; Harscoat-Schiavo, C.; Vanderesse, R.; Blanchard, F.; Fick, M. Process Biochem. 2010, 45, 382.
56. Aursand, M.; Grasdalen, H. Chem. Phys. Lipids 1992, 62, 239.
57. Enaud, E.; Humeau, C.; Piffaut, B.; Girardin, M. J. Mol. Catal. B: Enzym. 2004, 27, 1.
58. Chebil, L.; Anthoni, J.; Humeau, C.; Gerardin, C.; Engasser, J.-M.; Ghoul, M. J. Agric. Food Chem. 2007, 55, 9496.
59. Ziaullah. Bhullar, K. S.; Warnakulasuriya, S. N.; Rupasinghe, H. P. V. Bioorg. Med. Chem. 2013, 21, 684.
60. Vatèle, J.-M.; Fenet, B.; Eynard, T. Chem. Phys. Lipids 1998, 94, 239.
61. La Cara, F.; d'Auria, S.; Scarfi, M. R.; Zeni, O.; Massa, R.; d'Ambrioso, G.; Franceschetti, G.; De Rosa, M.; Rossi, M. Protein Pept. Lett. 1999, 6, 155.
62. Ponne, C. T.; Bartels, P. V. Radiat. Phys. Chem. 1995, 45, 591.
63. Mazumder, S.; Laskar, D. D.; Prajapati, D.; Roy, M. K. Chem. Biodivers. 2004, 1, 925.