Helvetica Chimica Acta ± Vol. 82 (1999)
1183
(
10), and dihexyl disulfide (11) were determined by GC with dibutyl sulfide as internal standard. N-
Methylaniline (7) was also determined by GC.
The reactions with the methylamines 12 ± 16 were performed analogously.
REFERENCES
[
1] C. L. Drennan, M. M. Dixon, D. M. Hoover, J. T. Jarrett, C. W. Goulding, R. G. Matthews, M. L. Ludwig, in
Vitamin B12 and B12-Proteinsꢁ, Eds. B. Kräutler, D. Arigoni, and B. T. Golding, Wiley-VCH, Weinheim,
998, p. 133.
ꢀ
1
[
[
[
[
[
[
[
[
2] C. W. Goulding, D. Postigo, R. G. Matthews, Biochemistry 1997, 36, 8082.
3] E. Stupperich, FEMS Microbiol. Rev. 1993, 12, 349.
4] R. J. Matthews, J. T. Drummond, Chem. Rev. 1990, 90, 1275.
5] R. V. Banerjee, R. G. Matthews, FASEB J. 1990, 4, 1450.
6] U. K. Pandit, Pure Appl. Chem. 1994, 66, 759.
7] E. Hillhorst, A. S. Iskander, T. B. R. A. Chen, U. K. Pandit, Tetrahedron Lett. 1993, 34, 4257.
8] J. M. Pratt, P. R. Norris, M. S. A. Hamza, R. Bolton, J. Chem. Soc., Chem. Commun. 1994, 1333.
9] J. M. Pratt, in ꢀMetal Ions in Biological Systemsꢁ, Eds. H. Siegel and A. Siegel, Marcel Dekker, Inc., New
York, 1993, Vol. 29, pp. 229 ± 286.
[
[
10] E. Stupperich, R. Konle, M. Lehle, in ꢀVitamin B12 and B12-Proteinsꢁ, Eds. B. Kräutler, D. Arigoni, and B. T.
Golding, Wiley-VCH, Weinheim, 1998, p. 179.
11] L. D. Zydowsky, T. M. Zydowsky, E. S. Haas, J. W. Brown, J. N. Reeve, H. G. Floss, J. Am. Chem. Soc. 1987,
1
09, 7922.
[12] J. C. Gonzales, K. Peariso, J. E. Penner-Hahn, R. G. Matthews, Biochemistry 1996, 35, 12228.
[13] K. Peariso, C. W. Goulding, S. Huang, R. G. Matthews, J. E. Penner-Hahn, J. Am. Chem. Soc. 1998, 120,
8
410.
[
[
[
14] W. Goulding, R. G. Matthews, Biochemistry 1997, 36, 15749.
15] P. van der Meijden, C. van der Drift, G. D. Vogels, Arch. Microbiol. 1984, 138, 360.
16] J. T. Jarrett, M. Amaratunga, C. L. Drennan, J. D. Scholten, R. H. Sands, M. L. Ludwig, R. G. Matthews,
Biochemistry 1996, 35, 2464.
[
[
[
[
[
[
[
17] K. Sauer, U. Harms, R. K. Thauer, Eur. J. Biochem. 1997, 243, 670.
18] E. Stupperich, in ꢀAcetogenesisꢁ, Ed. H. L. Drake, Chapman & Hall, New York, London, 1994, p. 180.
19] R. G. Matthews, C. W. Goulding, Curr. Opin. Chem. Biol. 1997, 332.
20] B. L. Vallee, D. S. Auld, Acc. Chem. Res. 1993, 26, 543.
21] L. C. Myers, M. P. Terranova, A. E. Ferentz, G. Wagner, G. L. Verdine, Science 1993, 261, 1164.
22] U. Brand, M. Rombach, H. Vahrenkamp, Chem. Commun. 1998, 2717.
23] J. F. Chlebowski, J. E. Coleman, in ꢀMetal Ions in Biological Systemsꢁ, Ed. H. Sigel, Marcel Dekker, Inc.,
New York, 1976, Vol. 6, pp. 1 ± 140; M. Kirchgessner, H.-P. Roth, in ꢀMetal Ions in Biological Systemsꢁ, Eds.
H. Sigel and A. Sigel, Marcel Dekker, Inc., New York, 1983, Vol. 15, Chapt. 9.
24] J. S. K. Shapiro, F. Schlenk, ꢀTransmethylation and Methionine Biosynthesisꢁ, The University of Chicago
Press, Vol. III, 1965.
[
[
[
[
25] G. N. Schrauzer, Angew. Chem. 1976, 88, 465.
26] G. N. Schrauzer, R. J. Windgassen, J. Am. Chem. Soc. 1967, 89, 3607.
27] M. Tada, Waseda University, Japan, personal communication, 1997.
[
[
[
[
[
[
[
[
28] A. Schnyder, T. Darbre, R. Keese, Angew. Chem. 1998, 110, 1301; ibid., Int. Ed. 1998, 37, 1283.
29] D. Zheng, T. Darbre, R. Keese, J. Inorg. Biochem. 1999, 73, 273.
30] G. N. Schrauzer, E. Deutsch, R. J. Windgassen, J. Am. Chem. Soc. 1968, 90, 2441.
31] A. W. Johnson, N. Shaw, F. Wagner, Biochim. Biophys. Acta 1963, 72, 107.
32] G. N. Schrauzer, Acc. Chem. Res. 1968, 1, 97.
33] G. N. Schrauzer, R. J. Windgassen, J. Am. Chem. Soc. 1967, 89, 3607.
34] G. N. Schrauzer, J. W. Siebert, R. J. Windgassen, J. Am. Chem. Soc. 1968, 90, 6681.
35] G. Agnes, H. A. O. Hill, J. M. Pratt, S. C. Ridsdale, F. S. Kennedy, R. J. P. Williams, Biochim. Biophys. Acta
1
971, 252, 207; P. R. Norris, J. M. Pratt, Biofactors 1995, 5, 240.
[
[
36] T. Frick, M. D. Fracia, J. M. Wood, Biochim. Biophys. Acta 1976, 428, 808.
37] H. P. C. Hogenkamp, G. T. Bratt, S.-Z. Sun, Biochemistry 1985, 24, 6428.