Synthesis of γ- and δ-Amino Acids

Amino Acids, Peptides and Proteins in Organic Chemistry

Volumn 1, Issue , 2010, Pages 527-571

  Trabocchi, Andrea ^a   Menchi, Gloria ^a   Guarna, Antonio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Asymmetric synthesis; Carbohydrate; Peptide; Peptide nucleic acid; Peptidomimetic

Indexed keywords

EID: 84885763712     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527631766.ch13     Document Type: Chapter

References (119)

1. Giannis, A. and Kolter, T. (1993) Angewandte Chemie (International Edition in English), 32, 1244.
2. Gante, J. (1994) Angewandte Chemie (International Edition in English), 33, 1699.
3. Abdel-Magid, A.F., Cohen, J.H., and Maryanoff, C.A. (1999) Current Medicinal Chemistry, 6, 955.
4. Juaristi, E. and Lopez-Ruiz, H. (1999) Current Medicinal Chemistry, 6, 983.
5. Sewald, N. (1996) Amino Acids, 11, 397.
6. Cole, D.C. (1994) Tetrahedron, 50, 9517.
7. Gellman, S.H. (1998) Accounts of Chemical Research, 31, 173.
8. Iverson, B.L. (1997) Nature, 385, 113.
9. Seebach, D. and Matthews, J.L. (1997) Journal of the Chemical Society, Chemical Communications, 2015.
10. Hanessian, S., Luo, X., Schaum, R., and Michnick, S. (1998) Journal of the American Chemical Society, 120, 8569.
11. Hintermann, T., Gademann, K., Jaun, B., and Seebach, D. (1998) Helvetica Chimica Acta, 81, 983.
12. Szabo, L., Smith, B.L., McReynolds, K.D., Parrill, A.L., Morris, E.R., and Gervay, J. (1998) The Journal of Organic Chemistry, 63, 1074.
13. Duke, R.K., Chebib, M., Hibbs, D.E., Mewett, K.N., and Johnston, G.A.R. (2004) Tetrahedron: Asymmetry, 15, 1745.
14. Allan, R.D., Bates, M.C., Drew, C.A., Duke, R.K., Hambley, T.W., Johnston, G.A.R., Mewett, K.N., and Spence, I. (1990) Tetrahedron, 46, 2511.
15. Hoveyda, A.H., Evans, D.A., and Fu, G.C. (1993) Chemical Reviews, 93, 1307.
16. Evans, D.A., Gage, J.R., Leighton, J.L., and Kim, A.S. (1992) The Journal of Organic Chemistry, 57, 1961.
17. Belliotti, T.R., Capiris, T., Ekhato, I.V., Kinsora, J.J., Field, M.J., Heffner, T.G., Meltzer, L.T., Schwarz, J.B., Taylor, C.P., Thorpe, A.J., Vartanian, M.G., Wise, L.D., Ti, Z.-S., Weber, M.L., and Wustrow, D.J. (2005) Journal of Medicinal Chemistry, 48, 2294.
18. Brenner, M. and Seebach, D. (1999) Helvetica Chimica Acta, 82, 2365.
19. Yuen, P.-W., Kanter, G.D., Taylor, C.P., and Vartanian, M.G. (1994) Bioorganic & Medicinal Chemistry Letters, 4, 823
20. Palomo, C., Aizpurua, J.M., Oiarbide, M., García, J.M., Gonzaléz, A., Odriozola, I., and Linden, A. (2001) Tetrahedron Letters, 42, 4829.
21. Palomo, C., Gonzaléz, A., García, J.M., Landa, C., Oiarbide, M., Rodríguez, S., and Linden, A. (1998) Angewandte Chemie (International Edition in English), 37, 180.
22. Camps, P., Munóz-Torrero, D., and Sánchez, L. (2004) Tetrahedron: Asymmetry, 15, 2039.
23. Zelle, R.E. (1991) Synthesis, 1023.
24. Wall, G.M. and Baker, J.K. (1989) Journal of Medicinal Chemistry, 32, 1340.
25. Ordóñez, M. and Cativiela, C. (2007) Tetrahedron: Asymmetry, 18, 3.
26. Bryans, J.S. and Wustrow, D.J. (1999) Medicinal Research Reviews, 19, 149.
27. Pardridge, W.M. (1985) Annual Reports in Medicinal Chemistry, 20, 305.
28. Shashoua, V.E., Jacob, J.N., Ridge, R., Campbell, A., and Baldessarini, R.J. (1984) Journal of Medicinal Chemistry, 27, 659.
29. Lippert, B., Metcalf, B.W., Jung, M.J., and Casara, P. (1977) European Journal of Biochemistry, 74, 441.
30. Allan, R.D., Bates, M.C., Drew, C.A., Duke, R.K., Hambley, T.W., Johnston, G.A.R., Mewett, K.N., and Spence, I. (1990) Tetrahedron, 46, 2511.
31. Olpe, H.-R., Demieville, H., Baltzer, V., Bencze, W.L., Koella, W.P., Wolf, P., and Haas, H.L. (1978) European Journal of Pharmacology, 52, 133.
32. Ong, J., Kerr, D.I.S., Doolette, D.J., Duke, R.K., Mewett, K.N., Allen, R.D., and Johnston, G.A.R. (1993) European Journal of Pharmacology, 233, 169.
33. Bryans, J.S., Davies, N., Gee, N.S., Dissanayake, V.U.K., Ratcliffe, G.S., Horwell, D.C., Kneen, C.O., Morrell, A.I., Oles, R.J., O'Toole, J.C., Perkins, G.M., Singh, L., Suman-Chauhan, N., and ONeill, J.A. (1998) Journal of Medicinal Chemistry, 41, 1838.
34. Burk, M.J., De Koning, P.D., Grote, T.M., Hoekstra, M.S., Hoge, G., Jennings, R.A., Kissel, W.S., Le, T.V., Lennon, I.C., Mulhern, T.A., Ramsden, J.A., and Wade, R.A. (2003) The Journal of Organic Chemistry, 68, 5731.
35. Thakur, V.V., Nikalje, M.D., and Sudalai, A. (2003) Tetrahedron: Asymmetry, 14, 581.
36. Mazzini, C., Lebreton, J., Alphand, V., and Furstoss, R. (1997) Tetrahedron Letters, 38, 1195.
37. Johannesen, S.A., Albu, S., Hazell, R.G., and Skrydstrup, T. (1962) Journal of the Chemical Society, Chemical Communications, 2004.
38. Tseng, C.C., Terashima, S., and Yamada, S.-I. (1977) Chemical & Pharmaceutical Bulletin, 25, 29.
39. Matthews, J.L., Braun, C., Guibourdenche, C., Overhand, M., and Seebach, D. (1997) In Enantioselective Synthesis of b-Amino Acids (ed. E. Juaristi), Wiley-VCH Verlag GmbH, Weinheim, pp. 105-126.
40. Buchschacher, P., Cassal, J.-M., Fürst, A., and Meier, W. (1977) Helvetica Chimica Acta, 60, 2747.
41. Dixon, D.J., Ley, S.V., and Rodríguez, F. (2001) Organic Letters, 3, 3753.
42. Reetz, M.T., Griebenow, N., and Goddard, R. (1995) Journal of the Chemical Society, Chemical Communications, 1605.
43. Adang, A.E.P., Hermkens, P.H.H., Linders, J.T.M., Ottenheijm, H.C.J., and van Staveren, C.J. (1994) Recueil des Travaux Chimiques des Pays-Bas, 113, 63.
44. Umezawa, H., Aoyagi, T., Morishima, H., Matsuzaki, M., Hamada, H., and Takeuchi, T. (1970) Journal of Antibiotics, 23, 259.
45. Hom, R.K., Fang, L.Y., Mamo, S., tung, J.S., Guinn, A.C., Walker, D.E., Davis, D.L., Gailunas, A.F., Thorsett, E. D., Leanna, M.R., DeMattei, J.A., Li, W., Nichols, P.J., Rasmussen, M., and Morton, E. (2000) Organic Letters, 2, 3627.
46. Sun, C.I., Chen, C.H., Kashiwada, Y., Wu, J.H., Wang, H.K., and Lee, K.H. (2002) Journal of Medicinal Chemistry, 45, 4271.
47. Thorsett, E.D., Sinha, S., Knops, J.E., Jewett, N.E. Anderson, J.P. and Varghese, J. (2003) Journal of Medicinal Chemistry, 46, 1799.
48. Liang, B., Richard, D.J., Portonovo, P.S., and Joullie, M.M. (2001) Journal of the American Chemical Society, 123, 4469.
49. Castejón, P., Moyano, A., Pericàs, M.A., and Riera, A. (1996) Tetrahedron, 52, 7063.
50. Kambourakis, S. and Rozzell, J.D. (2004) Tetrahedron, 60, 663.
51. Patel, R.N., Banerjee, A., Howell, J.M., McNamee, C.G., Brozozowski, D., Mirfakhrae, D., Nanduri, V., Thottathil, J.K., and Szarka, L.J. (1993) Tetrahedron: Asymmetry, 4, 2069.
52. Gou, D.M., Liu, Y.C., and Chen, C.S. (1993) The Journal of Organic Chemistry, 58, 1287.
53. Lu, Y., Miet, C., Kunesch, N., and Poisson, J.E. (1993) Tetrahedron: Asymmetry, 4, 893.
54. Lu, Y., Miet, C., Kunesch, N., and Poisson, J.E. (1990) Tetrahedron: Asymmetry, 1, 703.
55. Shioiri, T., Sasaki, S., and Hamada, Y. (2003) ARKIVOC, 103.
56. Sasaki, S., Hamada, Y., and Shioiri, T. (1999) Synlett, 453.
57. for the synthesis of diprotected (R)-GABOB from (S)-malic acid, see: Rajashekhar, B. and Kaiser, E.T. (1985) The Journal of Organic Chemistry, 50, 5480.
58. Smrcina, M., Majer, P., Majerová, E., Guerassina, T.A., and Eissenstat, M.A. (1997) Tetrahedron, 53, 12867.
59. Simonelli, F., Clososki, G.C., dos Santos, A.A., de Oliveira, A.R.M., Marques, F. de A., and Zarbin, P.H.G. (2001) Tetrahedron Letters, 42, 7375.
60. Martin, C.J., Rawson, D.J., and Williams, J.M.J. (1998) Tetrahedron: Asymmetry, 9, 3723.
61. Otaka, A., Yukimasa, A., Watanabe, J., Sasaki, Y., Oishi, S., Tamamura, H., and Fujii, N. (2003) Journal of the Chemical Society, Chemical Communications, 1834.
62. Gruner, S.A.W., Locardi, E., Lohof, E., and Kessler, H. (2002) Chemical Reviews, 102, 491.
63. Sanjayan, G.J., Stewart, A., Hachisu, S., Gonzalez, R., Watterson, M.P., and Fleet, G.W.J. (2003) Tetrahedron Letters, 44, 5847.
64. Gruner, S.A.W., Truffault, V., Voll, G., Locardi, E., Stöckle, M., and Kessler, H. (2002) Chemistry - A European Journal, 8, 4365.
65. Sofia, M.J., Hunter, R., Chan, T.Y., Vaughan, A., Dulina, R., Wang, H., and Gange, D. (1998) The Journal of Organic Chemistry, 63, 2802.
66. Burgess, K., Li, S., and Rebenspies, J. (1997) Tetrahedron Letters, 38, 1681.
67. Royer, F., Felpin, F.-X., and Doris, E. (2001) The Journal of Organic Chemistry, 66, 6487.
68. Okamoto, S., Teng, X., Fujii, S., Takayama, Y., and Sato, F. (2001) Journal of the American Chemical Society, 123, 3462.
69. Teng, X., Takayama, Y., Okamoto, S., and Sato, F. (1999) Journal of the American Chemical Society, 121, 11916.
70. El Marini, A., Roumestant, M.L., Viallefont, P., Razafindramboa, D., Bonato, M., and Follet, M. (1992) Synthesis, 1104.
71. Dexter, C.S. and Jackson, R.W.F. (1998) Journal of the Chemical Society, Chemical Communications, 75.
72. Mouriès, C., Deguin, B., Lamari, F., Foglietti, M.-J., Tillequin, F., and Koch, M. (2003) Tetrahedron: Asymmetry, 14, 1083.
73. Cordero, F.M., Pisaneschi, F., Batista, K.M., Valenza, S., Machetti, F., and Brandi, A. (2005) The Journal of Organic Chemistry, 70, 856.
74. Poitout, L., Le Merrer, Y., and Depezay, J.-C. (1995) Tetrahedron Letters, 36, 6887.
75. Chakraborty, T.K., Jayaprakash, S., Diwan, P.V., Nagaraj, R., Jampani, S.R.B., and Kunwar, A.C. (1998) Journal of the American Chemical Society, 120, 12962.
76. Chakraborty, T.K. and Ghosh, S. (2001) Journal of the Indian Institute of Science, 81, 117.
77. Long, D.D., Smith, M.D., Marquess, D.G., Claridge, T.D.W., and Fleet, G.W.J. (1998) Tetrahedron Letters, 39, 9293.
78. Smith, M.D., Long, D.D., Claridge, T.D.W., Fleet, G.W.J., and Marquess, D.G. (1998) Journal of the Chemical Society, Chemical Communications, 2039.
79. Smith, M.D., Claridge, T.D.W., Fleet, G.W.J., Tranter, G.E., and Sansom, M.S.P. (1998) Journal of the Chemical Society, Chemical Communications, 2041.
80. Watterson, M.P., Edwards, A.A., Leach, J.A., Smith, M.D., Ichihara, O., and Fleet, G.W.J. (2003) Tetrahedron Letters, 44, 5853.
81. VanWell, R.M., Meijer, M.E.A., Overkleeft, H.S., van Boom, J.H., van der Marel, G.A., and Overhand, M. (2003) Tetrahedron, 59, 2423.
82. Peri, F., Cipolla, L., La Ferla, B., and Nicotra, F. (2000) Journal of the Chemical Society, Chemical Communications, 2303.
83. Graf von Roedern, E., Lohof, E., Hessler, G., Hoffmann, M., and Kessler, H. (1996) Journal of the American Chemical Society, 108, 10156.
84. Suhara, Y., Yamaguchi, Y., Collins, B., Schnaar, R.L., Yanagishita, M., Hildreth, J.E.K., Shimada, I., and Ichikawa, Y. (2002) Bioorganic and Medicinal Chemistry, 10, 1999.
85. Graf von Roedern, E. and Kessler, H. (1994) Angewandte Chemie (International Edition in English), 33, 687.
86. Durrat, F., Xie, J., and Valéry, J.-M. (2004) Tetrahedron Letters, 45, 1477.
87. Baldauf, C., Günther, R., and Hofmann, H.-J. (2004) The Journal of Organic Chemistry, 69, 6214.
88. Gardner, R.R., Liang, G.-B., and Gellman, S.H. (1995) Journal of the American Chemical Society, 117, 3280.
89. Wipf, P., Henninger, T.C., and Geib, S.J. (1998) The Journal of Organic Chemistry, 63, 6088.
90. Belvisi, L., Colombo, L., Manzoni, L., Potenza, D., and Scolastico, C. (2004) Synlett, 1449.
91. Wang, W., Yang, J., Ying, J., Xiong, C., Zhang, J., Cai, C., and Hruby, V.J. (2002) The Journal of Organic Chemistry, 67, 6353.
92. Bravin, F.M., Busnelli, G., Colombo, M., Gatti, F., Manzoni, L., and Scolastico, C. (2004) Synthesis, 353.
93. Manzoni, L., Belvisi, L., Di Carlo, E., Forni, A., Invernizzi, D., and Scolastico, C. (2006) Synthesis, 1133.
94. Hanessian, S., McNaughton-Smith, G., Lombart, H.-G., and Lubell, W.D. (1997) Tetrahedron, 53, 12789.
95. Estiarte, M.A., Rubiralta, M., Diez, A., Thormann, M., and Giralt, E. (2000) The Journal of Organic Chemistry, 65, 6992.
96. Kim, K. and Germanas, J.P. (1997) The Journal of Organic Chemistry, 62, 2847.
97. Kim, K. and Germanas, J.P. (1997) The Journal of Organic Chemistry, 62, 2853.
98. Belvisi, L., Gennari, C., Mielgo, A., Potenza, D., and Scolastico, C. (1999) European Journal of Organic Chemistry, 389.
99. Salimbeni, A., Paleari, F., Canevotti, R., Criscuoli, M., Lippi, A., Angiolini, M., Belvisi, L., Scolastico, C., and Colombo, L. (1997) Bioorganic & Medicinal Chemistry Letters, 7, 2205.
100. Belvisi, L., Bernardi, A., Checchia, A., Manzoni, L., Potenza, D., Scolastico, C., Castorina, M., Cupelli, A., Giannini, G., Carminati, P., and Pisano F C. (2001) Organic Letters, 3, 1001.
101. Alonso, E., López-Ortiz, F., del Pozo, C., Peralta, E., Macías, A., and González, J. (2001) The Journal of Organic Chemistry, 66, 6333.
102. Khalil, E.M., Ojala, W.H., Pradhan, A., Nair, V.D., Gleason, W.B., Mishra, R.K., and Johnson, R.L. (1999) Journal of Medicinal Chemistry, 42, 628.
103. Genin, M.J. and Johnson, R.L. (1992) Journal of the American Chemical Society, 114, 8778.
104. Genin, M.J., Ojala, W.H., Gleason, W.B., and Johnson, R.L. (1993) The Journal of Organic Chemistry, 58, 2334.
105. Ecija, M., Diez, A., Rubiralta, M., and Casamitjana, N. (2003) The Journal of Organic Chemistry, 68, 9541.
106. Fink, B.E., Kym, P.R., and Katzenellenbogen, J.A. (1998) Journal of the American Chemical Society, 120, 4334.
107. Trabocchi, A., Menchi, G., Guarna, F., Machetti, F., Scarpi, D., and Guarna, A. (2006) Synlett, 331.
108. Trabocchi, A., Cini, N., Menchi, G., and Guarna, A. (2003) Tetrahedron Letters, 44, 3489.
109. Scarpi, D., Occhiato, E.G., Trabocchi, A., Leatherbarrow, R.J., Brauer, A.B.E., Nievo, M., and Guarna, A. (2001) Bioorganic and Medicinal Chemistry, 9, 1625.
110. Trabocchi, A., Occhiato, E.G., Potenza, D., and Guarna, A. (2002) The Journal of Organic Chemistry, 67, 7483.
111. Nielsen, P.E., Egholm, M., Berg, R.H., and Buchardt, O. (1991) Science, 254, 1497.
112. Hyrup, B. and Nielsen, P.E. (1996) Bioorganic and Medicinal Chemistry, 4, 5.
113. Uhlmann, E., Peyman, A., Breipohl, G., and Will, D.W. (1998) Angewandte Chemie (International Edition in English), 37, 2796.
114. Püschl, A., Tedeschi, T., and Nielsen, P.E. (2000) Organic Letters, 2, 4161.
115. Karig, G., Fuchs, A., Büsing, A., Brandstetter, T., Scherer, S., Bats, J.W., Eschenmoser, A., and Quinkert, G. (2000) Helvetica Chimica Acta, 83, 1049.
116. Schwalbe, H., Wermuth, J., Richter, C., Szalma, S., Eschenmoser, A., and Quinkert, G. (2000) Helvetica Chimica Acta, 83, 1079.
117. Casimir, J.R., Didierjean, C., Aubry, A., Rodriguez, M., Briand, J.-P., and Guichard, G. (2000) Organic Letters, 2, 895.
118. Grotenbreg, G.M., Christina, A.E., Buizert, A.E.M., van der Marel, G.A., Overkleeft, H.S., and Overhand, M. (2004) The Journal of Organic Chemistry, 69, 8331.
119. Brittain, D.E.A., Watterson, M.P., Claridge, T.D.W., Smith, M.D., and Fleet, G.W.J. (2000) Journal of the Chemical Society, Perkin Transactions 1, 3655.