Engineering carbohydrate scaffolds into the side chains of amino acids and use in combinatorial synthesis

Handbook of Carbohydrate Engineering

Volumn , Issue , 2005, Pages 749-780

  Schweizer, Frank ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85057238120     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (183)

1. Thompson, L.A. and Ellman, J., Chem. Rev., 96, 555, 1996.
2. Weiss, J.B., Lote, C.J., and Bobinski, H., Nature New Biol., 234, 25, 1971.
3. Lote, C.J. and Weiss, J.B., FEBS Lett., 16, 81, 1971.
4. Hofsteenge, J., Müller, D.R., Beer, T., Löffler, A., Richter, W.J., and Vliegenhart, J.F.G., Biochemistry, 33, 13524, 1994.
5. Beer, T., Vliegenhart, J.F.G., Löffler, A., and Hofsteenge, H., Biochemistry, 34, 117-85, 1995.
6. Löffler, A., Doucey, M.-A., Jansson, A.M., Müller, D.R., Beer, T., Hess, D., Meldal, M., Richter, W.J., Vliegenhart, J.F.G., and Hofsteenge, J., Biochemistry, 35, 12005, 1996.
7. Kreig, J., Hartmann, S., Vicentini, A., Gläsner, W., Hess, D., Hofsteenge, J., J. Mol. Biol. Cell, 9, 301, 1998.
8. Vliegenhart, J.F.G. and Casset, F., Curr. Opin. Struct. Biol., 8, 565, 1998.
9. Doucey, M.-A., Hess, D., Blommers, M.J.J., and Hofsteenge, J., Glycobiology, 9, 435, 1999.
10. Manabe, S. and Ito, Y., J. Am. Chem. Soc, 121, 9754, 1999.
11. Nishikawa, T., Ishikawa, M., and Isobe, M., Synlett, 123, 1999.
12. Manabe, S., Ito, Y., and Ogawa, T., Chem. Lett, 919, 1998.
13. Isono, K., J. Antibiot., 41, 1711, 1988 and references therein.
14. Nakajima, M., Itoi, K., Takamatsu, Y., Kinoshita, T., Okazaki, T., Kawakubo, K., Shindou, M., Hinma, T., Tohjigamori, M., and Haneishi, T., J. Antibiotics, 44, 293, 1991.
15. Van Well, R.M., Meijer, M.E.A., Overkleeft, H.S., Van Boom, J.H., van der Marel, G.A., and Overhand, M., Tetrahedron, 59, 2423, 2003.
16. Geyer, A., Bockelmann, D., Weissenbach, K., and Fischer, H., Tetrahedron Lett., 40, 477, 1999.
17. Geyer, A. and Moser, F., Eur. J. Org. Chem., 1113, 2000.
18. Tremmel, P. and Geyer, A., J. Am. Chem. Soc, 124, 8548, 2002.
19. Peri, F., Cipolla, L., La Ferla, B., and Nicotra, F., J. Chem. Soc. Chem. Commun., 2303, 2000.
20. Forni, E., Cipola, L., Caneva, E., La Ferla, B., Peri, F., and Nicotra, F., Tetrahedron Lett., 43, 1355, 2002.
21. Peri, F., Bassetti, R., Caneva, E., De Gioia, L., La Ferla, F., Presta, M., Tanghetti, E., and Nicotra, F., J. Chem. Soc. Perkin. Trans., I, 638, 2002.
22. Bartolozzi, A., Li, B., and Franck, R.W., Bioorg. Med. Chem, 11, 3021, 2003.
23. Palomo, C., Landa, A., Gonzalez-Regio, M.C., Garcia, J.M., Gonzalez, A., Odriozola, J. M., Martin-Pastor, M., and Linden, A., J. Am. Chem. Soc., 124, 8637, 2002.
24. Gruner, S.A.W., Keri, G., Schwab, R., Venetianer, A., and Kessler, H., Org. Lett., 3, 3723, 2001.
25. Dondoni, A. and Marra, A., Chem. Rev., 100, 4395, 2000.
26. Gruner, S.A.W., Locardi, E., Lohof, E., and Kessler, H., Chem. Rev, 102, 491, 2002.
27. Chakraborty, T.K., Ghosh, S., and Jayaprakash, J., Curr. Med. Chem, 9, 421, 2002.
28. Peri, F., Cipolla, L., Forni, E., and Nicotra, F., Monatsch. für Chemie, 133, 369, 2002.
29. Graf von Roedern, E., Lohof, E., Hessler, G., Hoffmann, M., and Kessler, H., J. Am. Chem. Soc., 118, 10156, 1996.
30. Graf von Roedern, E. and Kessler, H., Angew. Chem. Int. Ed. Engl., 33, 687, 1994.
31. Chakraborty, T.K., Jayaprakash, S., Diwan, P.V., Nagaraj, R., Jampani, S.R.B., and Kunwar, A.C., J. Am. Chem. Soc, 120, 12962, 1998.
32. Lohof, E., Planker, E., Mang, C., Burkhart, F., Dechantsreiter, M.A., Haubner, R., Wester, H.-J., Schwaiger, M., Hölzemann, G., Goodman, S.L., and Kessler, H., Angew. Chem. Int. Ed., 39, 2761, 2000.
33. Kriek, N.M.A.J., van der Hout, E., Kelly, P., van Meijgaarden, K.E., Geluk, A., Ottenhoff, T.H.M., van der Marel, G.A., Overhand, M., van Boom, J.H., Valentijn, A.R.P.M., and Overkleeft, H.S., Eur. J. Org. Chem, 2418, 2003.
34. Dwek, R.A., Chem. Rev., 96, 683, 1996.
35. Varki, A., Glycobiology, 3, 97, 1993.
36. Lee, Y.C. and Lee, R.T., Acc. Chem. Res, 28, 322, 1995.
37. McAuliffe, J.C. and Hindsgaul, O., Carbohydrates in medicine, in Molecular and Cellular Glycobiology, Frontiers in Molecular Biology, Vol. 10, Fukuda, M. and Hindsgaul, O., Eds., Oxford University Press, Oxford, pp. 249-285, 2000.
38. Grochee, F.C., Gramer, M.J., Andersen, D.C., Bahr, J.B., and Rasmusssen, J.R., in Frontier in Bioprocessing II, Todd, C.P., Sikdar, S.K., and Bier, M., Eds., American Chemical Society, Washington DC, p. 199, 1992.
39. Fisher, J.F., Harrison, A.W., Bundy, G.L., Wilkinson, K.F., Rush, B.D., and Ruwart, M.J., J. Med. Chem, 34, 3140,1991.
40. Mehta, S., Meldal, M., Duus, J.O., and Bock, K., J. Chem. Soc. Perkin. Trans, 1, 1445, 1999 and references therein.
41. Lis, H. and Sharon, N., Eur. J. Biochem., 218, 1, 1993.
42. Hase, S., Nishimura, H., Kawabata, S., Iwanaga, S., and Kenaka, T., J. Biol. Chem, 265, 1858, 1990.
43. Bock, K., Schuster-Kolbe, J., Altman, E., Allmaier, G., Stahl, B., Christian, R., Sletyr, U.B., and Messner, P., J. Biol. Chem, 269, 7137, 1994.
44. Marcaurelle, L.A. and Bertozzi, C.R., Chem. Eur. J, 5, 1384, 1999.
45. Bertozzi, C.R., Cook, D.G., Kobertz, W.R., Gonzalez-Sxarano, F., and Bednarski, M.D., J. Am. Chem. Soc, 114, 10639, 1992.
46. Urban, D., Skrydstrup, T., and Beau, J.-M., Chem. Commun, 955, 1998.
47. Campbell, A.D., Paterson, D.E., Raynham, T.M., and Taylor, R.J.K., Chem. Commun, 1599, 1999.
48. Ben, R.N., Orellana, A., and Ayra, P., J. Org. Chem, 63, 4817, 1998.
49. Dorgan, B.J. and Jackson, F.W., Synlett, 859, 1996.
50. Dondoni, A., Marra, A., and Massi, A., Tetrahedron, 54, 2827, 1998.
51. Dondoni, A., Marra, A., and Massi, A., Chem. Commun., 1741, 1998.
52. Bertozzi, C.R., Hoeprich, J.P.D., and Bednarski, M.D., J. Org. Chem, 57, 6092, 1992.
53. Fuchs, T. and Schmidt, R.R., Synthesis, 753, 1998.
54. Debenham, S.D., Debenham, J.S., Burk, M.J., and Toone, E.J., J. Am. Chem. Soc, 119, 9897, 1997.
55. Tedebark, U., Meldal, M., Panza, L., and Bock, K., Tetrahedron Lett, 39, 1815, 1998.
56. Gustafsson, T., Saxtin, M., and Kihlberg, J., J. Org. Chem, 68, 2506, 2003.
57. Käsebeck, L. and Kessler, H., Liebigs Ann./Recueil, 1, 165, 1997.
58. Gerz, M., Matter, H., and Kessler, H., Angew. Chem. Int. Ed. Engl., 32, 269, 1993.
59. Elofsson, M., Walse, B., and Kihlberg, J., Tetrahedron Lett, 32, 7613, 1991.
60. Monsigney, M.L.P., Delay, D., and Vaculik, M., Carbohydr. Res., 59, 589, 1977.
61. Nicolaou, K.C., Chucholowski, A., Dolle, R.E., and Randall, J.L., J. Chem. Soc. Chem. Commun, 1155, 1984.
62. Jobron, L. and Hummel, G., Org. Lett, 2, 2265, 2000.
63. Knapp, S. and Myers, D.S., J. Org. Chem., 67, 2995, 2002.
64. Cohen, S.B. and Halcomb, R.L., J. Am. Chem. Soc., 124, 2534, 2002.
65. Hoffmann, M., Burkhart, F., Hessler, G., and Kessler, H., Helv. Chim. Acta, 79, 1519, 1996.
66. Frey, O., Hoffmann, M., and Kessler, H., Angew. Chem. Int. Ed. Engl., 34, 2026, 1995.
67. Saha, U.K. and Roy, R., Tetrahedron Lett, 36, 3635, 1995.
68. Dondoni, A., Marra, A., and Massi, A., J. Org. Chem., 64, 933, 1999.
69. Burkhart, F., Hoffmann, M., and Kessler, H., Angew. Chem. Int. Ed. Engl., 36, 1191, 1997.
70. Lay, L., Meldal, M., Nicotra, F., Panza, L., and Russo, G., Chem. Commun, 1469, 1997.
71. Dondoni, A., Mariotti, G., and Marra, A., Tetrahedron Lett, 41, 3483, 2000.
72. Dondoni, A., Mariotti, G., and Marra, A., J. Org. Chem., 67, 4475, 2002.
73. Marcaurelle, L.A., Rodriguez, E.C., and Bertozzi, C.R., Tetrahedron Lett., 39, 8417, 1998.
74. Peri, F., Cipolla, L., Rescigno, M., La Ferla, B., and Nicotra, F., Bioconjugate Chem., 12, 325, 2001.
75. Cipolla, L., Rescigno, M., Leone, A., Peri, F., La Ferla, B., and Nicotra, F., Bioorg. Med. Chem. Lett, 10, 1639, 2002.
76. Marcaurelle, L.A. and Bertozzi, C.R., Tetrahedron Lett., 39, 7279, 1998.
77. Werner, R.M., Shokek, O., and Davis, J.T., J. Org. Chem, 62, 8243, 1997.
78. Davis, N.J. and Flitsch, S.L., Tetrahedron Lett, 32, 6793, 1991.
79. Wong, S.Y.C., Guile, G., Dwek, R., and Arsequell, G., Biochem. J., 300, 843, 1994.
80. Bengtsson, M., Broddefalk, J., Dahmen, J., Henriksson, K., Kihlberg, J., Lohn, H., Srinivasa, B.R., and Stenvall, K., Glycoconj. J, 15, 223, 1998.
81. Schweizer, F. and Inazu, T., Org. Lett., 3, 4115, 2001.
82. Dondoni, A., Junquera, F., Merchan, F.L., Merino, P., Schermann, M.-C., and Tejero, T., J. Org. Chem., 62, 5484, 1997.
83. Simchen, G. and Pürkner, E., Synthesis, 525, 1990.
84. Colombo, L., Casiraghi, G., and Pittalis, A.J., J. Org. Chem, 56, 3897, 1990.
85. Rosenthal, A. and Brink, A.J., J. Carbohydr. Nucleosides Nucleotides, 2, 343, 1975.
86. Vincent, S.P., Schleyer, A., and Wong, C.-H., J. Org. Chem, 65, 4440, 2000.
87. Lowary, T., Meldal, M., Helmboldt, A., Vasella, A., and Bock, K., J. Org. Chem, 63, 9657, 1998.
88. Pearce, A.J., Ramaya, S., Thorn, S.N., Bloomberg, G.B., Walter, D.S., and Gallagher, T., J. Org. Chem, 64, 5453, 1999.
89. Palomo, C., Landa, A., Gonzalez-Regio, M.C., Garcia, J.M., Gonzalez, A., Odriozola, J. M., Martin-Pastor, M., and Linden, A., J. Am. Chem. Soc., 124, 8637, 2002.
90. Bichard, J.C.F., Mitchell, E.P., Wormald, M.R., Watson, K.A., Johnson, L.N., Zographos, A.E., Koutra, D.D., Oikanomakos, N.G., and Fleet, G.W.J., Tetrahedron Lett., 36, 2145, 1995.
91. Somasak, L., Nagy, V., Docsa, T., Toth, B., and Gergely, P., Tetrahedron Asymmetry, 11, 405.
92. Osz, E., Somsak, L., Szilagyi, L., Kovacs, L., Docsa, D., Toth, B., and Gergely, P., Bioorg. Med. Chem. Lett, 9, 1385, 1999.
93. Krülle, T.M., Watson, K.A., Gregoriou, M., Johnson, L.N., Crook, N.S., Watkin, D.J., Griffiths, R.C., Nash, R.J., Tsitanou, K.E., Zographos, S.E., Oikonomakos, G., and Fleet, G.W.J., Tetrahedron Lett., 36, 8291, 1995.
94. Brandstetter, T.W., Wormald, M.R., Dwek, R.A., Butters, T.D., Platt, F.M., Tsitanou, K. E., Zographos, S.E., Oikonomakos, N.G., and Fleet, G.W.J., Tetrahedron Asymmetry, 7, 157, 1996.
95. Schweizer, F. and Hindsgaul, O., Synlett, 1743, 2001.
96. Schweizer, F., Lohse, A., Otter, A., and Hindsgaul, O., Synlett, 1434, 2001.
97. Ohrui, H., Kuzuhara, H., and Emoto, M., Tetrahedron Lett., 45, 4267, 1971.
98. Neka, T., Hashizume, T., and Nishimura, M., Tetrahedron Lett, 45, 95, 1971.
99. Coutrot, P., Grison, C., and Coutrot, F., Synlett, 393, 1998.
100. Vasella, A. and Voeffray, R., Helv. Chim. Acta, 65, 1134, 1982.
101. Garner, P. and Park, J.M., Tetrahedron Lett, 30, 5065, 1989.
102. Evina, C.M. and Guillerm, G., Tetrahedron Lett., 37, 163, 1996.
103. Garner, P. and Park, J.M., J. Org. Chem, 55, 3772, 1990.
104. Casiraghi, G., Colombo, L., Rassu, G., and Spanu, P., J. Org. Chem., 56, 6523, 1991.
105. Hadrami, M.E., Lavergne, J.-P., Viallefont, P.H., Chiaroni, A., Riche, C., and Hasnaoui, A., Synth. Commun, 23, 157, 1993.
106. Czernecki, S., Dieulesaint, A., and Valery, J.-M., J. Carbohydr. Chem., 5, 469, 1986.
107. Rosenthal, A. and Richards, C.M., Carbohydr. Res., 31, 331, 1973.
108. Rosenthal, A. and Shudo, K., J. Org. Chem., 26, 4391, 1972.
109. Rosenthal, A., Richards, C.M., and Shudo, K., Carbohydr. Res, 27, 353, 1973.
110. Nishimura, Y., Shitara, E., Adachi, H., Toyoshima, M., Nakajima, M., Okami, M., and Takeuchi, Y., J. Org. Chem, 65, 2, 2000.
111. Shilvock, J.P., Nash, R.J., Lloyd, J.D., Winters, A.L., Asano, N., and Fleet, G.W.J., Tetrahedron Asymmetry, 9, 3505, 1998.
112. Shilvock, J.P., Wheatley, J.R., Nash, R.J., Watson, A.A., Griffiths, R.C., Butters, R.C., Müller, M., Watkin, D.J., Winkler, D.A., and Fleet, G.W.J., J. Chem. Soc. Perkin. Trans, 1, 2735, 1999.
113. Umezawa, H., Aoyagi, T., Komiyama, T., Morishima, H., Hamada, M., and Takeuchi, T., J. Antibiot., 27, 963, 1974.
114. Nishimura, Y., Kudo, T., Kondo, S., and Takeuchi, T., J Antibiot, 45, 963, 1992.
115. Nishimura, Y., Wang, W., Kondo, S., Aoyagi, T., and Umezawa, H., J. Am. Chem. Soc, 110, 7249, 1988.
116. Fuchss, T. and Schmidt, R.R., Synthesis, 259, 2000.
117. Fuchs, E.F. and Lehmann, J., J. Chem. Ber., 108, 2254, 1975.
118. Fuchs, E.F. and Lehmann, J., J. Carbohydr. Res., 45, 135, 1975.
119. Fuchs, E.F. and Lehmann, J., J. Carbohydr. Res, 49, 267, 1975.
120. Nicolaou, K.C., Flörke, H., Egan, M.G., Barth, T., and Estevez, V.A., Tetrahedron Lett, 36, 1775, 1995.
121. Suhara, Y., Ichikawa, M., Hildreth, J.E.K., and Ichikawa, Y., Tetrahedron Lett., 37, 2549, 1996.
122. Suhara, Y., Hildreth, J.E.K., and Ichikawa, Y., Tetrahedron Lett., 37, 1575, 1996.
123. Sabesan, S., Tetrahedron Lett, 38, 3127, 1998.
124. Timmers, C.M., Turner, J.J., Ward, C.M., van der Marel, G.A., Kouwijzer, M.L.C.E., Grootenhuis, P.D.J., and van Boom, J.H., Chem. Eur. J, 3, 920, 1997.
125. Smith, M.D., Long, D.D., Martin, A., Marquess, D.D., Claridge, T.D.W., and Fleet, G.W.J., Tetrahedron Lett, 40, 2191, 1999.
126. Long, D.D., Hungerford, N.L., Smith, M.D., Brittain, D.E.A., Marquess, D.G., Claridge, T.S.W., and Fleet, G.W.J., Tetrahedron Lett, 40, 2195, 1999.
127. Gervay, J., Flaherty, T.M., and Nguyen, C., Tetrahedron Lett, 38, 1493, 1997.
128. Szabo, L., Smith, B.L., McReynolds, K.D., Parrill, A.L., Morris, E.R., and Gervay, J., J. Org. Chem, 63, 1074, 1998.
129. Claridge, T.D.W., Long, D.D., Hungerford, N.L., Aplin, R.T., Smith, M.D., Marquess, D.G., and Fleet, G.W.J., Tetrahedron Lett, 40, 2199, 1999.
130. Smith, M.D., Claridge, T.D.W., Tranter, G.E., Sansom, M.S.P., and Fleet, G.W.J., Chem. Commun., 2041, 1998.
131. Long, D.D., Smith, M.M., Marquess, D.G., Claridge, T.D.W., and Fleet, G.W.J., Tetrahedron Lett., 39, 9293, 1998.
132. Brittain, D.E.A., Watterson, M.P., Claridge, T.D.W., Smith, M.S., and Fleet, G.W.J., J. Chem. Soc. Perkin. Trans., 1, 3655, 2000.
133. Hungerford, N.L., Claridge, T.D.W., Watterson, M.P., Aplin, R.T., Moreno, A., and Fleet, G.W.J., J. Chem. Soc. Perkin. Trans., 1, 3666, 2000.
134. Long, D.D., Setz, R.J.E., Nash, R.J., Marquess, D.D., Lloyd, J.D., Winters, A.L., Asano, N., and Fleet, G.W.J., J. Chem. Soc. Perkin. Trans., 1, 901, 1999.
135. Chakraborty, T.K., Jayaprakash, S., Srinivasu, P., Chary, M.G., Diwan, P.V., Nagaraj, R., Sankar, A.R., and Kunwar, A.C., Tetrahedron Lett., 41, 8167, 2000.
136. Yoshimura, J., Ando, H., Sato, T., Tsuchida, S., and Hashimoto, H., Bull. Chem. Soc. Jpn., 49, 2511, 1976.
137. Müller, C., Kitas, E., and Wessel, H.P., J. Chem. Soc. Chem. Commun., 2425, 1995.
138. Wessel, H.P., Mitchell, C.M., Loboto, C.M., and Schmid, G., Angew. Chem. Int. Ed. Engl, 32, 1712.
139. Nishimura, S.-I., Shinnosuke, N., and Kuriko, Y., Chem. Commun, 617, 1998.
140. Nicolaou, K.C., Trujillo, J.L., and Chibale, K., Tetrahedron, 53, 8751, 1997.
141. Hirschmann, R., Nicolaou, K.C., Pietranico, S., Leahy, E.M., Salvino, J., Arison, B., Cichy, M.A., Spoors, P.G., Shakespeare, W.C., Sprengeler, P.A., et al., J. Am. Chem. Soc, 115, 12550, 1993.
142. Hirschmann, R., Hynes, J.J., Cichy-Knight, M.A., van Rijn, R.D., Sprengeler, P.A., Spoors, P.G., Shakespeare, W.C., Pietranico-Cole, S., Barbosa, J., Liu, J., et al., J. Med. Chem., 41, 1382, 1998.
143. Smith III, A.B., Sasho, S., Barwis, B.A., Sprengeler, P., Barbosa, J., Hirschmann, R., and Cooperman, B.S., Bioorg. Med. Chem. Lett., 8, 3133, 1998.
144. Polt, R., Porreca, F., Szabo, L.Z., Bilsky, E.J., Davis, P., Abbruscato, T.J., Davis, T.P., Horvath, R., Yamamura, H.I., and Hruby, V.J., Proc. Natl. Acad. Sci. USA, 91, 7114, 1994.
145. Bilsky, E.J., Egleton, R.D., Mitchell, S.A., Palian, M.M., Davis, P., Huber, J.D., Jones, H., Yamamura, H.I., Janders, J., Davis, T.P., Porreca, F., Hruby, V.J., and Polt, R., J. Med. Chem, 43, 2586, 2000.
146. Polt, R. and Palian, M.M., Drugs of the Future, 26, 561, 2001.
147. Palian, M.M., Bogouslavsky, V.I., O’Brien, D.F., and Polt, R., J. Am. Chem. Soc, 125, 5823, 2003.
148. Drouillat, B., Kellam, B., Dekany, G., Starr, M.S., and Toth, I., Bioorg. Med. Chem. Lett, 7, 2247, 1997.
149. Overkleeft, H.S., Verhelst, S.H.L., Pieterman, E., Meeuwenoord, N.J., Overhand, M., Cohen, L.H., van der Marel, G.A., and van Boom, J.H., Tetrahedron Lett., 40,4103,1999.
150. McDevitt, J.P. and Lansbury, P.T., J. Am. Chem. Soc., 118, 3818, 1996.
151. Nilsson, U.J., Fournier, E.J.-L., and Hindsgaul, O., Bioorg. Med. Chem., 6, 1563, 1998.
152. Dömling, A. and Ugi, I., Angew. Chem. Int. Ed. Engl., 39, 3168, 2000.
153. Ugi, I., Angew. Chem. Int. Ed. Engl., 21, 810, 1982.
154. Wong, C.-H., Ye, X.-S., and Zhang, Z., J. Am. Chem. Soc, 120, 7137, 1998.
155. Wunberg, T., Kallus, C., Opatz, T., Henke, S., Schmidt, W., and Kunz, H., Angew. Chem. Int. Ed, 37, 2503, 1998.
156. Kallus, C., Opatz, T., Wunberg, W., Schmidt, W., Henke, S., and Kunz, H., Tetrahedron Lett, 40, 7783, 1999.
157. Opatz, T., Kallus, C., Wunberg, T., Schmidt, W., Henke, S., and Kunz, H., Eur. J. Org. Chem, 8, 1527, 2003.
158. Opatz, T., Kallus, C., Wunberg, W., Schmidt, W., Henke, S., and Kunz, H., Carbohydr. Res., 337, 2089, 2002.
159. Dinh, T.Q., Smith, C.D., Du, X., and Armstrong, R.W., J. Med. Chem, 41, 981, 1998.
160. Streicher, B. and Wünsch, B., Eur. J. Org. Chem., 6, 115, 2001.
161. Sofia, M.J., Hunter, R., Chan, T.Y., Vaughan, A., Dulina, R., Wang, H., and Gange, D., J. Org. Chem, 63, 2802, 1998.
162. Ghosh, M., Dulina, R.R., Kakarla, R., and Sofia, M.J., J. Org. Chem, 65, 8387, 2000.
163. Sofia, M.J., Allanson, N., Hatzenbuhler, N.T., Jain, R., Kakarla, R., Kogan, N., Liang, R., Liu, D., Silva, D.J., Wang, H., et al., J. Med. Chem, 42, 3193, 1999.
164. Barkley, A. and Arya, P., Chem. Eur. J, 7, 555, 2001.
165. Hilaire, P.M.S.T. and Meldal, M., Angew. Chem. Int. Ed, 39, 1162, 2000.
166. Sofia, M.J., Mol. Divers, 3, 75, 1998.
167. St. Hilaire, P.M., Lowary, T.L., Meldal, M., and Bock, K., J. Am. Chem. Soc., 120, 13312, 1998.
168. Jobron, L. and Hummel, G., Angew. Chem. Int. Ed., 39, 1621, 2000.
169. Lampe, T.F.J., Weitz-Schmidt, G., and Wong, C.-H., Angew. Chem. Int. Ed., 37, 1707, 1998.
170. Burton, J.W., Son, J.C., Fairbanks, A.J., Choi, S.S., Taylor, H., Watkin, D.J., Winchester, B.G., and Fleet, G.W.J., Tetrahedron Lett, 34, 6119, 1993.
171. Brandstetter, T.W., Kim, Y.-H., Son, J.C., Taylor, H.M., Lilley, P.M., Watkin, D.J., Johnson, L.N., Oikonomakos, N.G., and Fleet, G.W.J., Tetrahedron Lett., 36, 2149, 1995.
172. Estevez, J.C., Smith, M.D., Lane, A.L., Crook, S., Watkin, D.J., Besra, G.S., Brennan, PJ., Nash, R.J., and Fleet, G.W.J., Tetrahedron Asymmetry, 7, 387, 1996.
173. Estevez, J.C., Estevez, R.J., Ardon, H., Wormald, M.R., Brown, D., and Fleet, G.W.J., Tetrahedron Lett., 35, 8885, 1994.
174. Brandstetter, T.W., de la Fuente, C., Kim, Y.-H., Johnson, L.N., Crook, S., deLilley, P.M., Watkin, D.J., Tsitanou, K.E., Zographos, S.E., Chrysina, E.D., Oikonomakos, N.G., and Fleet, G.W.J., Tetrahedron, 52, 10721, 1996.
175. Estevez, J.C., Long, D.D., Wormald, M.R., Dwek, R.A., and Fleet, G.W.J., Tetrahedron Lett., 36, 8287,1995.
176. Fleet, G.W.J., Estevez, J.C., Smith, M.D., Blerot, Y., de la Fuente, C., Krülle, T.M., Besra, G.S., Brennan, PJ., Nash, R.J., Johnson, L.N., Oikonomakos, N.G., and Stalmans, W., Pure Appl. Chem., 70, 279, 1998.
177. Lohse, A., Schweizer, F., and Hindsgaul, O., Combinatorial Chemistry &High Throughput Screening, 5, 389, 2002.
178. Lee, R.E., Smith, M.D., Pickering, L., and Fleet, G.W.J., Tetrahedron Lett, 40, 8689, 1999.
179. Long, D.D., Frederiksen, S.M., Marquess, D.G., Lane, A.L., Watkin, D.J., Winkler, D.A., and Fleet, G.W.J., Tetrahedron Lett., 39, 6091, 1998.
180. Lohse, A., Jensen, K.B., Lundgren, K., and Bols, M., Bioorg. Med. Chem., 7, 1965, 1999.
181. Lohse, A., Jensen, K.B., and Bols, M., Tetrahedron Lett., 40, 3033, 1999.
182. Brygesen, E., Nielsen, J., Willert, M., and Bols, M., Tetrahedron Lett., 38, 5697, 1997.
183. Du, M. and Hindsgaul, O., Synlett, 395, 1997.