Catalytic Effect of Thioles in Oxidation of the Vinyl Group to Aldehyde in Chlorophyll a Derivatives

Dmitry V. Belykh,^@ and Ekaterina V. Ashikhmina

Institute of Chemistry, Komi Scientific Center, Russian Academy of Sciences, 167982 Syktyvkar, Russia

^@Corresponding author E-mail: belykh-dv@chemi.komisc.ru, belykh-dv@mail.ru

Macroheterocycles 2012 5(1) 56-58

DOI: 10.6060/mhc2012.110736b

It is shown that thiols act as catalysts in the oxidation of the vinyl group in chlorophyll a derivatives (methylpheophorbide a, methylpyropheophorbide a, 13-amides chlorin e₆) to the aldehyde by atmospheric oxygen.

mhc2012_t05n01_56-58.pdf (545.76 KB)

References

Click here to expand or collapse this section

1.Nyman E. S., Hynninen P. H. J. Photochem. Photobiol., B: Biology 2004, 73, 1-28.
http://dx.doi.org/10.1016/j.jphotobiol.2003.10.002

2. Sternberg E.D., Dolphin D., Brückner Tetrahedron 1998, 54, 4151-4202.
http://dx.doi.org/10.1016/S0040-4020(98)00015-5

3. Bregadze V.I., Sivaev I.B., Gabel D., Wöhrle D. J. Porphyrins Phthalocyanines 2001, 5, 767-781.
http://dx.doi.org/10.1002/jpp.544

4. Gryglik D, Miller J.S., Ledakowicz S. Solar Energy 2004, 77, 615-623.
http://dx.doi.org/10.1016/j.solener.2004.03.029

5. Amao Y., Komori T. Biosensors and Bioelectronics 2004, 19, 843-847.
http://dx.doi.org/10.1016/j.bios.2003.08.003

6. Amao Y., Yamada Y. Biosensors and Bioelectronics 2007, 22, 1561-1565.
http://dx.doi.org/10.1016/j.bios.2006.07.006

7. Alekseev A.S., Tkachenko N.V., Tauber A.Y., Hynninen P.H., Osterbacka R., Stubb H., Lemmetyinen H. Chem. Phys, 2002, 275, 243-251.
http://dx.doi.org/10.1016/S0301-0104(01)00515-8

8. Tkachenko N.V., Hynninen P.H., Lemmetyinen H. Chem. Phys. Lett, 1996, 261, 234-240.
http://dx.doi.org/10.1016/0009-2614(96)00945-1

9. Davis R.C., Ditson S.L., Fentiman A.F., Pearlstein R.M. J. Am. Chem. Soc. 1981, 103, 6823-6826.
http://dx.doi.org/10.1021/ja00413a007

10. Tamiaki H., Holzwarth A.R., Schaffner K. Photosynth. Res. 1994, 41, 245-251.
http://dx.doi.org/10.1007/BF02184165

11. Tamiaki H., Kouraba M. Tetrahedron. 1997, 53, 10677-10688.
http://dx.doi.org/10.1016/S0040-4020(97)00699-6

12. Goswami L.N., Ethirajan M., Dobhal M.P., Zhang M., Missert J.R., Shibata M., Kadish K.M., Pandey R.K. J. Org. Chem. 2009, 74, 568-579.
http://dx.doi.org/10.1021/jo8019237

13. Jaquinod L., Nucro D.J., Medforth C.J., Pandey R.K., Forsyth T.P., Olmstead M.M., Smith K.M. Angew. Chem. Int. Ed. Engl. 1996, 35, 1013-1016.
http://dx.doi.org/10.1002/anie.199610131

14. Sasaki S., Kotegawa Y., Tamiaki H. Tetrahedron Lett. 2006, 47, 4849-4852.
http://dx.doi.org/10.1016/j.tetlet.2006.05.026

15. Sasaki S., Mizutani K., Kunieda M., Tamiaki H. Tetrahedron Lett. 2008, 49, 4113-4115.
http://dx.doi.org/10.1016/j.tetlet.2008.04.128

16. Johnson D.G., Niemczyk M.P., Minsek D.W., Wiederrecht G.P., Svec W.A., Gaines III G.L., Wasielewski M.R. J. Am. Chem. Soc. 1993, 115, 5692-5701.
http://dx.doi.org/10.1021/ja00066a039

17. Zheng G., Pandey R.K., Forsyth T.P., Kozyrev A.N., Dougherty T.J., Smith, K.M. Tetrahedron Lett. 1997, 38, 2409-2412.
http://dx.doi.org/10.1016/S0040-4039(97)00369-9

18. Pavlov V.Y., Ponomarev G.V. Chem. Heterocycl. Compd. 2004, 40, 393-425.
http://dx.doi.org/10.1023/B:COHC.0000033531.25694.2e

19. Fischer R., Engel N., Henseler A., Gossauer A. Helv. Chem. Acta. 1994, 77, 1046-1050.
http://dx.doi.org/10.1002/hlca.19940770417

20. Horn S., Dahms K., Senge M.O. J. Porphyrins Phthalocyanines 2008, 12, 1053-1077.
http://dx.doi.org/10.1142/S108842460800042X

21. Holt A.S., Morley H.V. Can. J. Chem. 1959, 37, 507-514.
http://dx.doi.org/10.1139/v59-069

22. Oba T., Uda Y., Matsuda K., Fukusumi T., Ito S., Hiratani K., Tamiaki H. Bioorg. Med. Chem. Lett. 2011, 21, 2489-2491
http://dx.doi.org/10.1016/j.bmcl.2011.02.054

23. Mathieu J., Panico R. Mécanismes réactionnels en chimie organique. Paris: Hermann, 1972, 765 p.

24. Waters W.A. Mechanisms of oxidation of organic compounds. New-York: John Wiley and sons, 1964. 152 p.

25. Ma L., Dolphin D. Tetrahedron. 1996, 52, 849-860.
http://dx.doi.org/10.1016/0040-4020(95)00944-2

26. Smith K.M., Goff D.A., Simpson D.J. J. Am. Chem. Soc. 1985, 107, 4946-4954.
http://dx.doi.org/10.1021/ja00303a021

27. Belykh D.V, Tarabukina I.S., Gruzdev I.V., Kodess M.I., Kutchin A.V. J. Porphyrins Phthalocyanines. 2009, 13, 949–956.
http://dx.doi.org/10.1142/S1088424609001133

28. Belykh D.V., Kopylov E.A., Gruzdev I.V., Kuchin A.V. Russ. J. Org. Chem. 2010, 46, 577-585.
http://dx.doi.org/10.1134/S1070428010040238

29. Belykh D.V., Buravlev E.V., Mal′shakova M.V., Parshukova N.N., Kopylov E.A., Gruzdev I.V., Kuchin A.V. Chem. Nat. Compd. 2011, 47, 85-90.
http://dx.doi.org/10.1007/s10600-011-9836-1

30. Tamiaki H., Miyata S., Kureishi Y., Tanikaga R. Tetrahedron, 1996, 52, 12421-12432.
http://dx.doi.org/10.1016/0040-4020(96)00740-5

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search