Deuterium and tritium labelling of N-acyl-L-homoserine lactones (AHLs) by catalytic reduction of a double bond in the layer-by-layer method

European Journal of Organic Chemistry

Volumn , Issue 24, 2013, Pages 5323-5330

  Jakubczyk, Dorota ^a,b,c   Merle, Christian ^a,b   Brenner Weiss, Gerald ^b   Luy, Burkhard ^a,b   Bräse, Stefan ^a,b  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^c JOHN INNES CENTRE   (United Kingdom)

Author keywords

Isomers; Isotopic labeling; Lactones; Layered compounds; Reduction; Regioselectivity

Indexed keywords

EID: 84881670285     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300084     Document Type: Article

References (50)

1. N. Amara, R. Mashiach, R. D. Amar, P. Krief, S. A. H. Spieser, M. J. Bottomley, A. Aharoni, M. M. Meijler, J. Am. Chem. Soc. 2009, 131, 10610-10619.
2. M. Boyer, F. Wisniewski-Dye, FEMS Microbiol. Ecol. 2009, 70, 1-19.
3. N. Nanting, L. Minyong, J. Wang, B. Wang, Med. Res. Rev. 2009, 29, 65-124.
4. S. R. Chhabra, C. Harty, D. S. Hooi, M. Daykin, P. Williams, G. Telford, D. I. Pritchard, B. W. Bycroft, J. Med. Chem. 2003, 46, 97-104.
5. J. A. Olsen, R. Severinsen, T. B. Rasmussen, M. Hentzer, M. Givskov, J. Nielsen, Bioorg. Med. Chem. Lett. 2002, 12, 325-328.
6. J. W. Costerton, P. S. Stewart, E. P. Greenberg, Science 1999, 284, 1318-1320.
7. J. B. Lyczak, C. L. Cannon, G. B. Pier, Clin. Microbiol. Rev. 2002, 15, 194-222.
8. M. Cooley, S. R. Chhabra, P. Williams, Chem. Biol. 2008, 15, 1141-1147.
9. D. T. Hughes, V. Sperandio, Nat. Rev. Microbiol. 2008, 6, 111-120.
10. K. P. Rumbaugh, J. A. Griswold, A. N. Hamood, Microbes Infect. 2000, 2, 1721-1731.
11. S. Zimmermann, C. Wagner, W. Muller, G. Brenner-Weiss, F. Hug, B. Prior, U. Obst, G. M. Hansch, Infect. Immun. 2006, 74, 5687-5692.
12. Q. Wang, L. Liu, C. Lin, H. Sun, W. X. Zhang, Z. Xi, Dalton Trans. 2009, 10433-10435.
13. D. Jakubczyk, C. Barth, A. Kubas, F. Anastassacos, P. Koelsch, K. Fink, U. Schepers, G. Brenner-Weiß, S. Braäse, Anal. Bioanal. Chem. 2012, 403, 473-482.
14. A. E. Mutlib, Chem. Res. Toxicol. 2008, 21, 1672-1689.
15. A. T. Tran, V. A. Huynh, E. M. Friz, S. K. Whitney, D. B. Cordes, Tetrahedron Lett. 2009, 50, 1817-1819.
16. H. C. Brown, C. A. Brown, J. Am. Chem. Soc. 1962, 84, 1493.
17. H. C. Brown, C. A. Brown, J. Am. Chem. Soc. 1962, 84, 1494.
18. C. A. Brown, J. Org. Chem. 1970, 35, 1900-1904.
19. C. A. Brown, V. K. Ahuja, J. Org. Chem. 1973, 38, 2226-2230.
20. S. Yakabe, M. Hirano, T. Morimoto, Tetrahedron Lett. 2000, 41, 6795-6798.
21. P. K. Sharma, S. Kumar, P. Kumar, P. Nielsen, Tetrahedron Lett. 2007, 48, 8704-8708.
22. J. M. Tour, J. P. Cooper, S. L. Pendalwar, J. Org. Chem. 1990, 55, 3452-3453.
23. J. Y. Wang, G. H. Song, Y. Q. Peng, Y. D. Zhu, Tetrahedron Lett. 2008, 49, 6518-6520.
24. V. I. Simagina, P. A. Storozhenko, O. V. Netskina, O. V. Komova, G. V. Odegova, T. Y. Samoilenko, A. G. Gentsler, Kinet. Catal. 2007, 48, 168-175.
25. J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. 2007, 119, 7890; Angew. Chem. Int. Ed. 2007, 46, 7744-7765.
26. J. M. Herbert, J. Labelled Compd. Radiopharm. 2010, 53, 658.
27. Y. Sawama, Y. Monguchi, H. Sajiki, Synlett 2012, 23, 959-972.
28. J. Atzrodt, V. Derdau, J. Labelled Compd. Radiopharm. 2010, 53, 674-685.
29. R. Voges, J. R. Heys, T. Moenius, Preparation of compounds labelled with tritium and carbon-14, Wiley, Chichester, 2009.
30. V. Derdau, J. Atzrodt, Synlett 2006, 1918-1922.
31. V. Derdau, J. Atzrodt, W. Holla, J. Labelled Compd. Radiopharm. 2007, 50, 295-298.
32. V. Derdau, J. Atzrodt, J. Zimmermann, C. Kroll, F. Brückner, Chem. Eur. J. 2009, 15, 10397-10404.
33. T. R. Bosin, M. G. Raymond, A. R. Buckpitt, Tetrahedron Lett. 1973, 47, 4699-4700.
34. G. E. Calf, J. L. Garnett, J. Phys. Chem. 1964, 68, 3887-3889.
35. G. E. Calf, J. L. Garnett, J. Catal. 1964, 3, 461-465.
36. W. Schmitz, R. Fingerhut, E. Conzelmann, Eur. J. Biochem. 1994, 222, 313-323.
37. G. Schwarzmann, Biochim. Biophys. Acta 1978, 529, 106-114.
38. R. Birk, G. Brenner-Weiß, A. Giannis, K. Sandhoff, R. R. Schmidt, J. Labelled Compd. Radiopharm. 1991, 29, 289-298.
39. M. F. Rastegar, G. W. Buchanan, M. C. Bouffard, J. Fluorine Chem. 2006, 127, 1042-1045.
40. A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136.
41. F. A. J. Meskens, Synthesis 1981, 501.
42. M. J. Kantam, V. N. P. Sreekanthn, Catal. Commun. 2001, 2, 301-304.
43. E. L. Eliel, J. K. Koskimies, B. Lohri, J. Am. Chem. Soc. 1978, 100, 1614-1616.
44. W. Willker, D. Leibfritz, R. Kerssebaum, W. Bermel, Magn. Reson. Chem. 1993, 31, 287-292.
45. T. Skinner, T. Reiss, B. Luy, N. Khaneja, S. J. Glaser, J. Magn. Reson. 2003, 163, 8-15.
46. T. E. Skinner, T. O. Reiss, B. Luy, N. Khaneja, S. J. Glaser, J. Magn. Reson. 2004, 167, 68-74.
47. K. Kobzar, T. Skinner, N. Khaneja, S. J. Glaser, B. Luy, J. Magn. Reson. 2004, 170, 236-243.
48. K. Kobzar, T. E. Skinner, N. Khaneja, S. J. Glaser, B. Luy, J. Magn. Reson. 2008, 194, 58-66.
49. K. Kobzar, S. Ehni, T. E. Skinner, S. J. Glaser, B. Luy, J. Magn. Reson. 2012, 225, 142-160.
50. Dyeing Reagents for Thin Layer and Paper Chromatography, E. Merck, Darmstadt, Germany, 1974.