Synthesis of disulfides containing a corrinoid head group for preparation of self-assembled monolayers

Synlett

Volumn , Issue 12, 2005, Pages 1901-1904

  Mendonça, Joana ^a   Luginbühl, Reto ^a   Siegenthaler, Hans ^a   Keese, Reinhart ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Cobester disulfides; Disulfides; Self assembled monolayers; Vitamin B12 derivatives

Indexed keywords

BIS[COALPHA,COBETA DI(CYANO KAPPAC) N C,N C (DITHIODIDECAN 10,1 DIYL)]BIS[COB(III)YRINIC ACID C AMIDE A,B,D,E,F,G HEXAMETHYL ESTER; COALPHA,COBETA DI(CYANO KAPPAC) N C (11,12 DITHIODOCOSAN 1 YL)COB(III)YRINIC ACID C AMIDE A,B,D,E,F,G HEXAMETHYL ESTER; COALPHA,COBETA DI(CYANO KAPPAC) N C (11,12 DITHIOOCTADEC 1 YL)COB(III)YRINIC ACID C AMIDE A,B,D,E,F,G HEXAMETHYL ESTER; CORRINOID; CYANOCOBALAMIN; DISULFIDE; ESTER DERIVATIVE; GOLD; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SPECTROSCOPY; SYNTHESIS; TIME OF FLIGHT MASS SPECTROMETRY;

EID: 23644453076     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871941     Document Type: Article

References (54)

1. Surface Analysis: The Principal Techniques; Vickerman, J. C., Ed.; J. Wiley and Sons Ltd.: Chichester, 2003.
2. Bubert, H.; Holger, J. Surface and Thin Film Analysis: A Compendium of Principles, Instrumentation and Applications; Wiley-VCH: Weinheim, 2002.
3. Godin, M.; Laroche, O.; Tabard-Cossa, V.; Beaulieu, L. Y.; Grutter, P.; Williams, P. J. Rev. Sci. Instrum. 2003, 74, 4902.
4. Imaging of Surfaces and Interfaces; Lipkowski, J.; Ross, P. N., Eds.; Wiley-VCH: Weinheim, 1999.
5. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103.
6. Multilayer Thin Films; Decher, G.; Schlenoff, J. B., Eds.; Wiley-VCH: Weinheim, 2003.
7. Potyrailo, R. A. Macromol. Rapid Commun. 2004, 25, 78.
8. Huang, J.; Virji, S.; Weiller, B. H.; Kaner, R. B. Chem.-Eur. J. 2004, 10, 1315.
9. Lee, D. W.; Swager, T. M. Synlett 2004, 149.
10. Janata, J.; Josowicz, M. Nature Materials 2003, 2, 19.
11. Spichiger-Keller, U. E. Chimia 2003, 57, 317.
12. Mikrosysteme - Nanosysteme, Bull. Swiss Fed. Inst. of Techn./Zürich, No. 292, Feb. 2004.
13. Wroblewski, W.; Dybko, A.; Malinowska, E.; Brzozka, Z. Talanta 2004, 63, 33.
14. Calvo-Munoz, M. L.; Truong, T. T.; Tran-Thi, T. H. Sens. Actuators, B 2002, 87, 173.
15. Eggins, B. R. Chemical Sensors and Biosensors; J. Wiley and Sons: New York, 2002.
16. Cosnier, S. Anal. Bioanal. Chem. 2003, 377, 507.
17. Cosnier, S.; Gondran, C.; Wessel, R.; Montforts, F.-P.; Wedel, M. Sensors 2003, 3, 213.
18. 12, Biochemistry and Medicine, Vol. 1 and 2; Dolphin, D., Ed.; Wiley-Interscience: New York, 1982.
19. 12-Proteins; Kräutler, B.; Arigoni, D.; Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998.
20. 12; Wiley: New York, 1999.
21. Holliger, C.; Wohlfahrt, G.; Diekert, G. FEMS Rev. 1999, 22, 383.
22. Matthews, R. G. Acc. Chem. Res. 2001, 34, 681.
23. Stubbe, J. Chem. Commun. 2003, 20, 2511.
24. (a) He, M.; Dowd, P. J. Am. Chem. Soc. 1996, 118, 711.
25. (b) He, M.; Dowd, P. J. Am. Chem. Soc. 1998, 120, 1133.
26. Pratt, J. M. In Handbook of Metalloproteins; Bertini, I.; Sigel, A.; Sigel, H., Eds.; Marcel Dekker Inc.: New York, 2001, Chap. 13.
27. Buckel, W.; Golding, B. T. Chem. Soc. Rev. 1996, 25, 329.
28. Wolleb-Gygi, A.; Darbre, T.; Siljegovic, V.; Keese, R. J. Chem. Soc., Chem. Commun. 1994, 835.
29. Shimakoshi, H.; Nakazato, A.; Hayashi, T.; Tachi, Y.; Naruta, Y.; Hisaeda, Y. J. Electroanalyt. Chem. 2001, 507, 170.
30. Zheng, D.; Darbre, T.; Keese, R. J. Inorg. Biochem. 1999, 73, 273.
31. Wedemeyer-Exl, C.; Darbre, T.; Keese, R. Helv. Chim. Acta 1999, 82, 1173.
32. McKauly, K. M.; Wilson, S. R.; van der Donk, W. A. Inorg. Chem. 2002, 41, 393.
33. Gao, J.; Rusling, J. F.; Zhou, D. J. Org. Chem. 1996, 61, 5972.
34. Darbre, T.; Siljegovic, V.; Amolins, A.; Otten, T.; Keese, R.; Abrantes, L.; Correia, J. P. In Novel Trends in Electroorganic Synthesis; Torii, S., Ed.; Springer Verlag: Tokyo, 1998, 395.
35. Darbre, T.; Zheng, D.; Fraga, R.; Keese, R. In Electrochem. Soc. Proc. 2000, 15, 53.
36. Ruhe, A.; Walder, L.; Scheffold, R. Helv. Chim. Acta 1985, 68, 1301.
37. Steiger, B.; Ruhe, A.; Walder, L. Anal. Chem. 1990, 62, 759.
38. Caro, C. A.; Bedioui, F.; Zagal, J. H. Electrochim. Acta 2002, 47, 1489.
39. Cardenas-Jiron, G. I.; Gulppi, M. A.; Caro, C. A.; del Rio, R.; Paez, M.; Zagal, J. H. Electrochim. Acta 2001, 46, 3227.
40. Fraga, R.; Coirreia, J. P.; Keese, R.; Abrantes, L. M. Electrochim. Acta 2005, 50, 1653.
41. Viana, A. S.; Kalaji, M.; Abrantes, L. M. Electrochim. Acta 2002, 47, 1587.
42. Fraga, R. PhD Thesis; University of Lisboa: Portugal, 2004.
43. Ahuja, D. K.; Gavalas, V. G.; Bachas, L. G.; Bhattacharyya, D. Ind. Eng. Chem. Res. 2004, 43, 1049.
44. Pfammatter, M.; Siljegovic, V.; Darbre, T.; Keese, R. Helv. Chim. Acta 2001, 84, 678.
45. Still, I. W. J.; Kutney, G. W.; McLean, D. J. Org. Chem. 1982, 47, 560.
46. Wolfe, S. R.; Miller, M. J. J. Org. Chem. 1986, 51, 3133.
47. Buckel, F.; Person, P.; Effenberger, F. Synthesis 1995, 1126.
48. Akiyama, M.; Katoh, A.; Ogawa, T. J. Chem. Soc., Perkin Trans. 2 1989, 1213.
49. Lau, J.; Pedersen, E. B.; Jensen, L. V. Arch. Pharm. 1991, 324, 83.
50. Szöcs, E.; Durrer, L.; Luginbühl, R.; Simic, N.; Viana, A.; Abrantes, L.; Keese, R.; Siegenthaler, H., manuscript in preparation.
51. 12, Biochemistry and Medicine, Vol. 1; Dolphin, D., Ed.; Wiley-Interscience: New York, 1982, Chap. 7, 226.
52. (a) Stepanek, R. PhD Thesis; ETH Zürich: Switzerland, 1987, no. 8069.
53. (b) Caderas, C. PhD Thesis; ETH Zürich: Switzerland, 1987, no. 7822.
54. Wolleb-Gygi, A. PhD Thesis; University of Bern: Switzerland, 1993.