Synthesis of N-Alkyl Amino Acids

Amino Acids, Peptides and Proteins in Organic Chemistry

Volumn 1, Issue , 2010, Pages 245-289

  Aurelio, Luigi ^a   Hughes, Andrew B ^b  

^a MONASH UNIVERSITY   (Australia)

^b LA TROBE UNIVERSITY   (Australia)

Author keywords

1,3 oxazolidin 5 ones; Alkylation; N alkyl amino acids; N methyl amino acids; Reductive amination

Indexed keywords

EID: 84885814148     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527631766.ch6     Document Type: Chapter

References (127)

1. Hughes, E., Burke, R.M., and Doig, A.J. (2000) The Journal of Biological Chemistry, 275, 25109.
2. Doig, A.J., Hughes, E., Burke, R.M., Su, T.J., Heenan, R.K., and Lu, J. (2002) Biochemical Society Transactions, 30, 537.
3. Mason, J.M., Kokkoni, N., Stott, K., and Doig, A.J. (2003) Current Opinion in Structural Biology, 13, 526.
4. Gordon, D.J., Tappe, R., and Meredith, S.C. (2002) The Journal of Peptide Research, 60, 37.
5. Kapurniotu, A., Schmauder, A., and Tenidis, K. (2002) Journal of Molecular Biology, 315, 339.
6. Fairlie, D.P., Abbenante, G., and March, D.R. (1995) Current Medicinal Chemistry, 2, 654.
7. Ostresh, J.M., Husar, G.M., Blondelle, S., Dorner, B., Weber, P.A., and Houghten, R.A. (1994) Proceedings of the National Academy of Sciences of the United States of America, 91, 11138.
8. Miller, S.M., Simon, R.J., Ng, S., Zuckermann, R.N., Kerr, J.M., and Moos, W.H. (1995) Drug Development Research, 35, 20.
9. Turker, R.K., Hall, M.M., Yamamoto, M., Sweet, C.S., and Bumpus, F.M. (1972) Science, 177, 1203.
10. Haviv, F., Fitzpatrick, T.D., Swenson, R.E., Nichols, C.J., Mort, N.A., Bush, E.N., Diaz, G., Bammert, G., Nguyen, A., Rhutasel, N.S., Nellans, H.N., Hoffman, D.J., Johnson, E.S., and Greer, J. (1993) Journal of Medicinal Chemistry, 36, 363.
11. Cody, W.L., He, J.X., Reily, M.D., Haleen, S.J., Walker, D.M., Reyner, E.L., Stewart, B.H., and Doherty, A.M. (1997) Journal of Medicinal Chemistry, 40, 2228.
12. Payne, J.W. (1972) Journal of General Microbiology, 71, 259.
13. Fischer, E. and Lipschitz, W. (1915) Chemische Berichte, 48, 360.
14. Fischer, E. and Mechel, L.V. (1916) Chemische Berichte, 49, 1355.
15. Izumiya, N. and Nagamatsu, A. (1952) Bulletin of the Chemical Society of Japan, 25, 265.
16. Winstein, S. (1939) Journal of the American Chemical Society, 61, 1635
17. Winstein, S. and Lucas, H.J. (1939) Journal of the American Chemical Society, 61, 2845
18. Brewster, P., Hiron, F., Hughes, E.D., Ingold, C.K., and Rao, P.A.D.S. (1950) Nature, 166, 179.
19. Grossman, R.B. (1999) The Art of Writing Reasonable Organic Reaction Mechanisms, Springer, New York.
20. Izumiya, N. (1952) Kyushu Memoirs of Medical Science, 3, 1
21. Izumiya, N. (1951) Journal of the Chemical Society of Japan (Nippon Kagaku Zasshi), 72, 550
22. Izumiya, N. (1951) Journal of the Chemical Society of Japan (Nippon Kagaku Zasshi), 72, 784
23. Izumiya, N. (1951) Journal of the Chemical Society of Japan (Nippon Kagaku Zasshi), 72, 26
24. Izumiya, N. (1951) Journal of the Chemical Society of Japan (Nippon Kagaku Zasshi), 72, 700.
25. Effenberger, F., Burkard, U., and Willfahrt, J. (1986) Liebigs Annalen der Chemie, 314.
26. Quitt, P., Hellerbach, J., and Vogler, K. (1963) Helvetica Chimica Acta, 46, 327
27. Quitt, P. (1963) In Peptides: Proceedings of the 5th European Symposium, Pergamon, Oxford, p. 165.
28. Hlavácek, J., Poduska, K., Sorm, F., and Sláma, K. (1976) Collection of Czechoslovak Chemical Communications, 41, 2079.
29. Hlavácek, J., Fric, I., Budesinsky, M., and Bláha, K. (1988) Collection of Czechoslovak Chemical Communications, 53, 2473.
30. Miller, S.C. and Scanlan, T.S. (1997) Journal of the American Chemical Society, 119, 2301.
31. Albanese, D., Landini, D., Lupi, V., and Penso, M. (2000) European Journal of Organic Chemistry, 1443.
32. Biron, E. and Kessler, H. (2005) The Journal of Organic Chemistry, 70, 5183.
33. Di Gioia, M.L., Leggio, A., Le Pera, A., Liguori, A., Napoli, A., Siciliano, C., and Sindona, G. (2003) The Journal of Organic Chemistry, 68, 7416
34. Belsito, E., Di Gioia, M.L., Greco, A., Leggio, A., Liguori, A., Perri, F., Siciliano, C., and Viscomi, M.C. (2007) The Journal of Organic Chemistry, 72, 4798.
35. Das, B.C., Gero, S.D., and Lederer, E. (1967) Biochemical and Biophysical Research Communications, 29, 211.
36. Olsen, R.K. (1970) The Journal of Organic Chemistry, 35, 1912.
37. Okamoto, K., Abe, H., Kuromizu, K., and Izumiya, N. (1974) Memoirs of the Faculty of Science, Kyushu University - Series C, 9, 131.
38. Tam, J.P., Spetzler, J.C., and Rao, C. (1993) In Peptides: Biology and Chemistry: Proceedings of the Chinese Peptide Symposium, ESCOM, Leiden, p. 285.
39. Coggins, J.R. and Benoiton, N.L. (1971) Canadian Journal of Chemistry, 49, 1968
40. Cheung, S.T. and Benoiton, N.L. (1977) Canadian Journal of Chemistry, 55, 906.
41. Benoiton, N.L., Kuroda, K., Cheung, S.T., and Chen, F.M.F. (1979) Canadian Journal of Biochemistry, 57, 776.
42. McDermott, J.R. and Benoiton, N.L. (1973) Canadian Journal of Chemistry, 51, 2555.
43. McDermott, J.R. and Benoiton, N.L. (1973) Canadian Journal of Chemistry, 51, 2562.
44. McDermott, J.R. and Benoiton, N.L. (1973) Canadian Journal of Chemistry, 51, 1915.
45. Coulton, S., Moore, G.A., and Ramage, R. (1976) Tetrahedron Letters, 4005.
46. Stoochnoff, B.A. and Benoiton, N.L. (1973) Tetrahedron Letters, 21.
47. Belagali, S.L., Mathew, T., and Himaja, M. (1995) Indian Journal of Chemistry Section B - Organic Chemistry Including Medicinal Chemistry, 34, 45.
48. Burger, K. and Hollweck, W. (1994) Synlett, 751.
49. Prashad, M., Har, D., Hu, B., Kim, H.-Y., Repic, O., and Blacklock, T.J. (2003) Organic Letters, 5, 125.
50. Liu, S., Gu, W., Lo, D., Ding, X.-Z., Ujiki, M., Adrian, T.E., Soff, G.A., and Silverman, R.B. (2005) Journal of Medicinal Chemistry, 48, 3630.
51. Papaioannou, D., Athanassopoulos, C., Magafa, V., Karamanos, N., Stavropoulos, G., Napoli, A., Sindona, G., Aksnes, D.W., and Francis, G.W. (1994) Acta Chemica Scandinavica, 48, 324.
52. Mitsunobu, O. (1981) Synthesis, 1.
53. Olah, G.A. and Narang, S.C. (1982) Tetrahedron, 38, 2225.
54. Wisniewski, K. and Kolodziejczyk, A.S. (1997) Tetrahedron Letters, 38, 483.
55. Yang, L. and Chiu, K. (1997) In Proceedings of the 15th American Peptide Symposium, Kluwer, Boston, MA, p. 341
56. Yang, L. and Chiu, K. (1997) Tetrahedron Letters, 38, 7307.
57. Chruma, J.J., Sames, D., and Polt, R. (1997) Tetrahedron Letters, 38, 5085.
58. Ohfune, Y., Kurokawa, N., Higuchi, N., Saito, M., Hashimoto, M., and Tanaka, T. (1984) Chemistry Letters, 441
59. Ohfune, Y., Higuchi, N., Saito, M., Hashimoto, M., and Tanaka, T. (1984) Peptide Chemistry, 89.
60. Ramanjulu, J.M. and Joullié, M.M. (1996) Synthetic Communications, 26, 1379.
61. Rückle, T., Dubray, B., Hubler, F., and Mutter, M. (1999) Journal of Peptide Science, 5, 56.
62. Keller-Schierlein, W., Hagmann, L., Zähner, H., and Huhn, W. (1988) Helvetica Chimica Acta, 71, 1528.
63. Bowman, R.E. and Stroud, H.H. (1950) Journal of the Chemical Society, 1342.
64. Bowman, R.E. (1950) Journal of the Chemical Society, 1346.
65. Bowman, R.E. (1950) Journal of the Chemical Society, 1349.
66. Ikutani, Y. (1968) Bulletin of the Chemical Society of Japan, 41, 1679.
67. Poduska, K. (1958) Chemicke Listy, 52, 153.
68. Ebata, M., Takahashi, Y., and Otsuka, H. (1966) Bulletin of the Chemical Society of Japan, 39, 2535.
69. Brockmann, H. and Lackner, H. (1967) Chemische Berichte, 100, 353.
70. Eloff, J.N. (1980) Zeitschrift fur Pflanzenphysiologie, 98, 411.
71. Peter, H., Brugger, M., Schreiber, J., and Eschenmoser, A. (1963) Helvetica Chimica Acta, 46, 577.
72. O'Donnell, M.J., Bruder, W.A., Daugherty, B.W., Liu, D., and Wojciechowski, K. (1984) Tetrahedron Letters, 25, 3651.
73. Jentoft, N. and Dearborn, D.G. (1983) Methods in Enzymology, 91, 570.
74. Lane, C.F. (1975) Synthesis, 135.
75. Kaljuste, K. and Undén, A. (1993) International Journal of Peptide and Protein Research, 42, 118.
76. Hanson, R.W. and Law, H.D. (1965) Journal of the Chemical Society, 7285.
77. Chen, F.M.F. and Benoiton, N.L. (1977) Canadian Journal of Chemistry, 55, 1433.
78. Krishnamurthy, S. (1982) Tetrahedron Letters, 23, 3315.
79. McKennon, M.J., Meyers, A.I., Drauz, K., and Schwarm, M. (1993) The Journal of Organic Chemistry, 58, 3568.
80. Chu, K.S., Negrete, G.R., and Konopelski, J.P. (1991) The Journal of Organic Chemistry, 56, 5196.
81. Hall, D.G., Laplante, C., Manku, S., and Nagendran, J. (1999) The Journal of Organic Chemistry, 64, 698.
82. Ben-Ishai, D. (1957) Journal of the American Chemical Society, 79, 5736.
83. Itoh, M. (1969) Chemical & Pharmaceutical Bulletin, 17, 1679.
84. Allevi, P., Cighetti, G., and Anastasia, M. (2001) Tetrahedron Letters, 42, 5319.
85. Freidinger, R.M., Hinkle, J.S., Perlow, D.S., and Arison, B.H. (1983) The Journal of Organic Chemistry, 48, 77.
86. Auerbach, J., Zamore, M., and Weinreb, S.M. (1976) The Journal of Organic Chemistry, 41, 725.
87. Cipens, G., Slavinskaya, V.A., Sile, D., Korchagova, E.K., Katkevich, M.Y., and Grigoreva, V.D. (1992) Khimiya Geterotsiklicheskikh Soedinenii, 681.
88. Aurelio, L., Brownlee, R.T.C., Hughes, A.B., and Sleebs, B.E. (2000) Australian Journal of Chemistry, 53, 425
89. Aurelio, L., Brownlee, R.T.C., and Hughes, A.B. (2002) Organic Letters, 4, 3767
90. Aurelio, L., Box, J.S., Brownlee, R.T.C., Hughes, A.B., and Sleebs, M.M. (2003) The Journal of Organic Chemistry, 68, 2652.
91. Reddy, G.V., Rao, G.V., and Iyengar, D.S. (1998) Tetrahedron Letters, 39, 1985
92. Reddy, G.V. and Iyengar, D.S. (1999) Chemistry Letters, 299.
93. Williams, R.M. and Yuan, C. (1994) The Journal of Organic Chemistry, 59, 6190.
94. Willuhn, M., Platzek, J., Ottow, E., Petrov, O., Borm, C., Hinz, D., Mann, G., Lister-James, J., and Wilson, D.M. (2003) PCT WO03042163.
95. Luke, R.W.A., Boyce, P.G.T., and Dorling, E.K. (1996) Tetrahedron Letters, 37, 263.
96. Spengler, J. and Burger, K. (1998) Synthesis, 67
97. Burger, K. and Spengler, J. (2000) European Journal of Organic Chemistry, 199
98. Burger, K., Spengler, J., Hennig, L., Herzschuh, R., and Essawy, S.A. (2000) Monatshefte fur Chemie, 131, 463.
99. Yamashiro, D., Aanning, H.L., Branda, L.A., Cash, W.D., Murti, V.V.S., and Du Vigneaud, V. (1968) Journal of the American Chemical Society, 90, 4141.
100. Liu, J.-F., Tang, X.-X., and Jiang, B. (2002) Synthesis, 1499.
101. Ratner, S. and Clarke, H.T. (1937) Journal of the American Chemical Society, 59, 200.
102. Ruggles, E.L., Flemer, S. Jr., and Hondal, R.J. (2008) Biopolymers, 90, 61.
103. Zhang, S., Govender, T., Norström, T., and Arvidsson, P.I. (2005) The Journal of Organic Chemistry, 70, 6918
104. Govender, T. and Arvidsson, P.I. (2006) Tetrahedron Letters, 47, 1691.
105. Poisel, H. and Schmidt, U. (1973) Chemische Berichte, 106, 3408.
106. Pandey, G., Reddy, P.Y., and Das, P. (1996) Tetrahedron Letters, 37, 3175.
107. Agami, C., Couty, F., Hamon, L., Prince, B., and Puchot, C. (1990) Tetrahedron, 46, 7003.
108. Agami, C., Couty, F., Prince, B., and Puchot, C. (1991) Tetrahedron, 47, 4343.
109. Oppolzer, W., Cintas-Moreno, P., Tamura, O., and Cardinaux, F. (1993) Helvetica Chimica Acta, 76, 187.
110. Myers, A.G., Gleason, J.L., Yoon, T., and Kung, D.W. (1997) Journal of the American Chemical Society, 119, 656.
111. Grieco, P.A. and Bahsas, A. (1987) The Journal of Organic Chemistry, 52, 5746.
112. Dorow, R.L. and Gingrich, D.E. (1995) The Journal of Organic Chemistry, 60, 4986.
113. Laplante, C. and Hall, D.G. (2001) Organic Letters, 3, 1487.
114. Larsen, S.D., Connell, M.A., Cudahy, M.M., Evans, B.R., May, P.D., Meglasson, M.D., O'Sullivan, T.J., Schostarez, H.J., Sih, J.C., Stevens, F.C., Tanis, S.P., Tegley, C.M., Tucker, J.A., Vaillancourt, V.A., Vidmar, T.J., Watt, W., and Yu, J.H. (2001) Journal of Medicinal Chemistry, 44, 1217.
115. Guerrero, T.H. and Deulofeu, V. (1937) Chemische Berichte, 70, 947.
116. Alonso, D.A., Costa, A., and Nájera, C. (1997) Tetrahedron Letters, 38, 7943.
117. Groeger, U., Drauz, K., and Klenk, H. (1992) Angewandte Chemie (International Edition in English), 31, 195.
118. Gal, E.M. (1949) Journal of the American Chemical Society, 71, 2253.
119. Yang, C.-T., Vetrichelvan, M., Yang, X., Moubaraki, B., Murray, K.S., and Vittal, J.J. (2004) Journal of The Chemical Society, Dalton Transactions, 113.
120. Ando, A. and Shioiri, T. (1989) Tetrahedron, 45, 4969.
121. Bitan, G., Muller, D., Kasher, R., Gluhov, E.V., and Gilon, C. (1997) Journal of the Chemical Society, Perkin Transactions 1, 1501.
122. Fukuyama, T., Jow, C.-K., and Cheung, M. (1995) Tetrahedron Letters, 36, 6373.
123. Bhatt, U., Mohamed, N., Just, G., and Roberts, G. (1997) Tetrahedron Letters, 38, 3679.
124. Bowman, W.R. and Coghlan, D.R. (1997) Tetrahedron, 53, 15787.
125. Meerwein, H., Hinz, G., Hofmann, P., Kroning, E., and Pfeil, E. (1937) Journal fur Praktische Chemie, 147, 257.
126. Kadyrov, R., Riermeier, T.H., Dingerdissen, U., Tararov, V., and Börner, A. (2003) The Journal of Organic Chemistry, 68, 4067.
127. Schedel, H. and Burger, K. (2000) Monatshefte fur Chemie, 131, 1011.