Syntheses and monolayer properties of vitamin B12 derivatives with seven alkyl chains

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 169, Issue 1-3, 2000, Pages 47-58

  Ariga, Katsuhiko ^a   Tanaka, Keizo ^a   Katagiri, Kiyofumi ^a   Kikuchi, Jun Ichi ^a   Ohshima, Eiji ^b   Hisaeda, Yoshio ^b  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

Coordination; Monolayer; Orientation; Vitamin B12; A Isotherm

Indexed keywords

COBALT; COMPACTION; ESTERS; ISOTHERMS; LIPIDS; MATHEMATICAL MODELS; MOLECULAR ORIENTATION; MONOLAYERS; OXIDATION; PRESSURE EFFECTS; SYNTHESIS (CHEMICAL);

ALKYL CHAINS; HEPTAOCTYL ESTERS; HEPTAPROPYL ESTERS; SURFACE PRESSURE MOLECULAR AREA ISOTHERMS; VITAMIN B12 DERIVATIVE;

VITAMINS;

COBALT; CYANOCOBALAMIN; ESTER; LYSINE;

ARTICLE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033999410     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0927-7757(00)00416-7     Document Type: Article

References (57)

1. Smith E.L., Parker L.F.G. Biochem. J. 43:1948;396.
2. Ricks E.L., Brink N.G., Koniuszy F.R., Wood T.R., Folkers K. Science. 107:1948;396.
3. Barker H.A., Weissbach H., Smith R.D. Proc. Natl. Acad. Sci. USA. 44:1958;1093.
4. Lenhert P.G., Hodgkin D.C. Nature. 192:1961;937.
5. Fischili A., Daly J.J. Helv. Chim. Acta. 63:1980;1628.
6. Drennan C.L., Huang S., Drummond J.T., Matthews R.G., Luclwig M.L. Science. 266:1994;1669.
7. Ludwig M.L., Drennan C.L., Matthews R.G. Structure. 4:1996;509.
8. Mancia F., Keep N.H., Nakagawa A., Leadlay P.F., McSweeney S., Rasmussen B., Bosecke P., Diat O., Evans P.R. Structure. 4:1996;339.
9. Banerjee R. Chem. Biol. 4:1997;175.
10. Huang R.R., Grabowski J.J. J. Am. Chem. Soc. 121:1999;1359.
11. Dong S., Padmakumar R., Maiti N., Banerjee R., Spiro T.G. J. Am. Chem. Soc. 120:1998;9947.
12. Dong S., Padmakumar R., Banerjee R., Spiro T.G. J. Am. Chem. Soc. 118:1996;9182.
13. He M., Dowd P. J. Am. Chem. Soc. 120:1998;1133.
14. Brown K.L., Li J. J. Am. Chem. Soc. 120:1998;9466.
15. Walker L.A. II, Jarrett J.T., Anderson N.A., Pullen S.H., Mattfews R.G., Sension R.J. J. Am. Chem. Soc. 120:1998;3597.
16. Sirovatka J.M., Finke R.G. J. Am. Chem. Soc. 119:1997;3057.
17. Garr C.D., Sirovatka J.M., Finke R.G. J. Am. Chem. Soc. 118:1996;11142.
18. Gerfen G.J., Licht S., Willems J.-P., Hoffman B.M., Stubbe J. J. Am. Chem. Soc. 118:1996;8192.
19. Halpern J. Science. 227:1985;869.
20. Buckel W., Golding B.T. FEMS Microbiol. Rev. 22:1999;523-541.
21. Woodward R.B. Pure Appl. Chem. 33:1973;145.
22. Zhou D.-L., Njue C.K., Rusling J.F. J. Am. Chem. Soc. 121:1999;2909.
23. Mbindyo J.K.N., Rusling J.F. Langmuir. 14:1998;7027.
24. Zhou D.-L., Carrero H., Rusling J.F. Langmuir. 12:1996;3067.
25. Aga H., Aramata A., Hisaeda Y. J. Electroanal. Chem. 437:1997;111.
26. Zagal J.H., Aguirre M.J., Paez M.A. J. Electroanal. Chem. 437:1997;45.
27. Y. Murakami, Y. Hisaeda, T. Ozaki, Y. Matsuda, J. Chem. Soc. Chem. Commun., (1989) 1094.
28. Halpern J. Dolphin D. B12. 1:1982;501 Wiley, New York.
29. Schrauzer G.N. Acc. Chem. Res. 1:1968;97.
30. Elliot C.M., Herschenhart H., Finke R.G., Smith B.L. J. Am. Chem. Soc. 103:1981;5558.
31. Murakami Y., Aoyama Y., Tokunaga K. J. Am. Chem. Soc. 102:1980;6736.
32. Costa G. Cood. Chem. Rev. 8:1997;63.
33. Murakami Y., Hisaeda Y., Fan S.-D., Masuda Y. Bull. Chem. Soc. Jpn. 62:1989;2219.
34. Murakami Y., Kikuchi J., Hisaeda Y., Ohno T. Murakami Y. Comprehensive Supramolecular Chemistry. 4:1996;415 Pergamon, Oxford.
35. Hisaeda Y., Ogawa A., Ohno T., Murakami Y. Inorg. Chim. Acta. 273:1998;299.
36. Murakami Y., Hisaeda Y., Ogawa A., Ohno T. J. Chem. Soc. Perkin Trans. 2:1995;189.
37. Ohno T., Ogawa A., Hisaeda Y., Murakami Y. J. Chem. Soc. Perkin Trans. 2:1994;2271.
38. Ohno T., Ogawa A., Hisacda Y., Murakami Y. Tetrahedron Lett. 35:1994;9589.
39. Y. Murakami, Y. Hisaeda, A. Ogawa, T. Ohno, Chem. Lett., (1994) 1657.
40. Murakami Y., Hisacda Y., Song X.-M., Ohno T. J. Chem. Soc. Perkin Trans. 2:1992;1527.
41. Murakami Y., Hisaeda Y., Ohno T. J. Chem. Soc. Perkin Trans. 2:1991;405.
42. Murakami Y., Hisaeda Y., Ohno T. Bull. Chem. Soc. Jpn. 57:1984;2091.
43. Murakami Y., Hisaeda Y., Kajihara A. Bull. Chem. Soc. Jpn. 56:1983;3642.
44. I,. Werthemann, R. Keese, A. Eschenmoser, unpublished results; see L. Werthemann, Dissertation, ETH Zurich (Nr. 4097), Juris Druck und Verlag, Zurich, 1968.
45. Rappe A.K., Casewit C.J., Colwell K.S., Goddard W.A. III, Skiff W.M. J. Am. Chem. Soc. 114:1992;10024.
46. Matsuzawa Y., Seki T., Ichimura K. Langmuir. 14:1998;4891.
47. Matsuzawa Y., Seki T., Ichimura K. Langmuir. 14:1998;683.
48. Baker S.M., Danzer J., Desaire H., Credo G., Flitton R. Langmuir. 14:1998;5267.
49. Bourgoin J.-P., Doublet F., Palacin S., Vandevyver M. Langmuir. 12:1998;6473.
50. Ariga K., Kunitake T., Furuta H. J. Chem. Soc. Perkin Trans. 2:1996;667.
51. Burghard M., Schmelzer M., Roth S., Haisch P., Hanack M. Langmuir. 10:1994;4266.
52. Azumi R., Matsumoto M., Kawabata Y., Kuroda S., Sugi M., King L.G., Crossley M.J. J. Phys. Chem. 97:1993;12862.
53. Fu Y., Jayaraj K., Lever A.B. Langmuir. 10:1994;3836.
54. Schick G.A., O'Grady M.R., Tiwari R.K. J. Phys. Chem. 97:1993;1339.
55. Desormeaux A., Ringuet M., Leclanc R.M. J. Colloid Interface Sci. 147:1991;57.
56. Gains G.L. Jr. Insoluble Monolayers at Liquid-Gas Interface. 1966;281 Interscience, New York.
57. J. Kikuchi, T. Takashima, H. Nakano, K. Hie, H. Etoh, Y. Noguchi, K. Suehiro, Y. Murakami, Chem. Lett. (1993) 553.