Recent advances in the synthesis of unnatural α-amino acids

Current Organic Chemistry

Volumn 11, Issue 9, 2007, Pages 801-832

  Perdih, A ^a   Dolenc, M Sollner ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Arylglycine derivatives; Dehydroamino acid derivatives; Hydrogenation; N Methylation; Proline derivatives; USP methodology

Indexed keywords

ALKYLATION; BIOCHEMISTRY; HYDROGENATION; MOLECULES; ORGANOMETALLICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ACID DERIVATIVE; AMINO ACID DERIVATIVES; AMINO-ACIDS; ARYLGLYCINE DERIVATIVE; DEHYDROAMINO ACID; DEHYDROAMINO ACID DERIVATIVE; N-METHYLATION; PROLINE DERIVATIVES; SYNTHETIC METHODS; USP METHODOLOGY;

AMINO ACIDS;

1,2 EPOXY 3 BUTENE; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALKANE DERIVATIVE; AMINO ACID DERIVATIVE; AROMATIC AMINO ACID; ASPARTIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DEHYDROALANINE; ESTER DERIVATIVE; FERROCENE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; GLYCINAMIDE; GLYCINE DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; HOMOSERINE; METHYLAMINE; ORGANOMETALLIC COMPOUND; OXAZINE DERIVATIVE; OXAZOLIDINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PENICILLAMINE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOXALINE DERIVATIVE; SERINE DERIVATIVE; SILANE DERIVATIVE; SULFONAMIDE; TRYPTOPHAN DERIVATIVE; UNINDEXED DRUG;

AMINO ACID SUBSTITUTION; ANTHELMINTIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CATALYST; CHIRALITY; DRUG DESIGN; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; INSECTICIDAL ACTIVITY; METHODOLOGY; ORGANIC CHEMISTRY; REVIEW; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS;

EID: 34250900985     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527207780831701     Document Type: Review

References (106)

1. Burger's Medicinal Chemistry and Drug Discovery, Volume 1, Drug Discovery, 6th Ed., John Wiley & Sons: New York, 2005.
2. Bonner, G.G.; Davis, P.; Stropova, C.; Ferguson, R.; Yamamura, H.I.; Porreca, F.; Hruby, V.J. Peptides,, 1997, 18, 93.
3. Marshall, S.A.; Lazar, G.A.; Chirino, A.; Desjarlais, J.R. Drug Discov. Today,, 2003, 8, 212.
4. Szymkowski, D.E. Drug Discov. Today, 2004, 9, 381.
5. Adessi, C.; Soto, C. Curr. Med. Chem., 2002, 9, 963.
6. Gante, J. Angew. Chem. Int. Ed. Engl., 1994, 33, 1699.
7. Marshall, G.R. Tetrahedron,, 1993, 49, 3547.
8. Wang, L.; Schultz, P.G. Chem. Commun., 2002, 43, 11623.
9. Maruoka, K.; Ooi, T. Chem. Rev., 2003, 103, 3013-3028.
10. Hendrickson,T.L.; Crécy-Lagard V.; Schimmel, P. Annu. Rev. Biochem., 2004, 73, 147.
11. Lu, V. Curr. Opin. Chem. Biol., 2005, 9, 118.
12. Beene, D.L.; Dougherty, D.A.; Lester, H.A. Curr. Opin. Neurobiol., 2003, 13, 267.
13. Hyun, M.H.; Han, S.C.; Lipshutz, B.H.; Shin, Y.-J.; Welch, C.J. J. Chromatogr. A, 2001, 910, 359.
14. Jin, J.S.; Stalcup, A.M.; Hyun, M.H. J. of Chromatogr. A, 2001, 933, 83.
15. Péter, A.; Árki, A.; Vékes, E.; Tourwé, D.; Lázár, L.; Fülöp, F.; Armstrong , D.W. J. Chromatogr. A, 2004, 1031, 171.
16. Gallos, J.K.; Sarli, V.C.; Massen, Z.S.; Varvogli, A.C.; Papadoyanni, C.Z.; Papaspyrou, S.D.; Argyropoulos, N.G. Tetrahedron, 2005, 46, 565.
17. Gallos, J.K.; Sarli, V. C.; Varvogli, A.C.; Papadoyanni, C.Z.; Papaspyrou, S.D.; Argyropoulos, N.G. Tetrahedron, 2003, 44, 3905.
18. Middleton, R.J.; Mellor, S.J.; Chhabra, S. R.; Bycroft, B. W.; Chan, W.C. Tetrahedron Lett., 2004, 45, 123.
19. Dygos, J.H., Yonan, E.E.; Scros, M.G.; Goodmonson, O.J.; Getman, D.P.; Periana, R.A.; Beck, G.R. Synthesis, 1992, 741.
20. Cheng, H.; Luzy, J.-P.; Garbay, C. Tetrahedron Lett., 2005, 46, 3319.
21. Boto, A.; Hernandez, R.; Montoya, A.; Suarez, E. Tetrahedron Lett., 2005, 43, 8.
22. Wasserman, H.H.; Long, Y.O.; Parr, J. Tetrahedron Lett., 2003, 44, 361.
23. Gorohovsky, S.; Meir, S.; Shkoulev, V.; Byk, G.; Gellerman, G. Synlett, 2003, 1411.
24. Carlier, P.; Lam, P.C.H.; Wong, D.M. J. Org. Chem., 2002, 67, 6256.
25. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett., 1996, 37, 5273.
26. Shieh, W.-C.; Xue, S.; Reel, N.; Wu, R.; Fitt, R.; Repič, O. Tetrahedron Asymmetry, 2001, 12, 2421.
27. Tanaka, K.; Ahn, M.; Watanabe, Y.; Fuji, K. Tetrahedron Asymmetry, 1996, 7, 1771.
28. Yu, G.; Mason, H.J.; Galdi, K.; Wu, X.; Cormelious, L.; Zhao, N.; Witkus, M.; Ewing, W.R.; Macor, J.E. Synthesis, 2003, 403.
29. Padrón, J.M.; Kokotos, G.; Martín, T.; Markidis, T.; Gibbons, W.A.; Martín V.A. Tetrahedron Asymmetry, 1998, 9, 3381.
30. Markidis, T.; Kokotos, G. J. Org. Chem., 2002, 67, 1685.
31. Wang, W.; Wang, J.; Li, H. Tetrahedron Lett., 2004, 45, 724.
32. Jingersons, A.; Marinozzi, M.; Pellicciari, R.; Tetrahedron, 2005, 61, 373.
33. Capone, S.; Guaragna, A.; Palumbo, G.; Pedatella, S. Tetrahedron,, 2005, 61, 6575.
34. Dondoni, A.; Massi, A.; Minghini, E.; Bertolasi, V. Tetrahedron,, 2004, 60, 2311.
35. Davis, F.A.; Zhang, Y.; Rao, A.; Zhang, Z. Tetrahedron, 2001, 57, 6345.
36. Huang, T.S.; Li, C. J. Org. Lett., 2001, 3, 2037.
37. Ballini, R.; Balsamini, C.; Bartoccini, F.; Gianotti, M.; Martinelli, C.; Savoretti, N. Synthesis, 2005, 2, 296.
38. Kim, H.J.; Lee, S.; Park, Y.S. Synlett, 2001, 5, 613.
39. Koskinen, A.M.P.; Hassilla, H.; Myllymäki, V.T.; Rissanen, K. Tetrahedron Lett., 1996, 36, 5619.
40. Park, C.; Choi, H.; Son, Y.-C.; Lee, C.S.; Choy, N.; Koh, J.S.; Lee, T.G.; Kwon, Y.D.; Kim, S.C.; Yoon, H. Biorg. Med. Chem., 1996, 6, 585.
41. Oba, M.; Tanaka, M.; Takano, Y.; Suemune, H. Tetrahedron, 2005, 61, 593.
42. Ellis, T.K.; Martin, C.H.; Tsai, G.H.; Ueki, H.; Soloshonok V.A. J. Org. Chem., 2003, 68, 6208.
43. Ueki, H.; Ellis, T.K.; Collin, M.H.; Soloshonok, V.A. Eur. J. Org.Chem., 2003, 1954.
44. Belokon, Y.N.; Bespalova, N.B.; Churkina, T.D.; Cisarova, I.; Ezernitskaya, M.G.; Harutyunyan, S.R.; Hrdina, R.; Kagan, H.B.; Kocovsky, P.; Kochetkov, K.A.; Larionov, O.V.; Lyssenko, K.A.; North, M.; Polasek, M.; Peregudov, A.S.; Prisyazhnyuk, V.V.; Vyskocil, S. J. Am. Chem. Soc., 2003, 125, 12860.
45. Miyabe, H.; Asada, R.; Takemoto, Y. Tetrahedron, 2005, 61, 385.
46. Warmuth, R.; Munsch, T.E.; Stalker, R.A.; Li, B.; Beatty, A. Tetrahedron, 2001, 57, 6383.
47. Chowdari, N.S.; Suri, J.T.; Barbas III, C.F. Org. Lett., 2004, 6, 2507.
48. van Esseveldt, B.C.J.; van Delft, F.L.; Smits, J.M.M.; de Gelder, R.; Rutjes, F.P.J.T. Synlett, 2003, 15, 2354-2358.
49. van Esseveldt, B.C.J.; van Delft, F.L.; de Gelder, R; Rutjes, F.P.J.T. Org. Lett., 2003, 5, 1717.
50. Cheng, W.-C.; Liu, Y.; Wong, M.; Olmstead, M.M.; Lam, K.S:; Kurth M.J. J. Org. Chem., 2002, 67, 5673.
51. Tiwari, S.K.; Schneider, A.; Koep, S.; Gais, H.-J. Tetrahedron Lett., 2004, 45, 8343.
52. Lautens, M.; Tayama, E.; Nguyen, D. Org. Lett., 2004, 6, 345.
53. Södergren, M.J.; Andersson P.G.; Tetrahedron Lett., 1996, 37, 7577.
54. Aurelio, L.; Brownlee, R.T.C.; Hughes, A.B. Chem. Rev., 2004, 104, 5823.
55. Biron, E.; Kessler, H. J. Org. Chem., 2005, 70, 5183.
56. White, K.N., Konopelski, J.P. Org. Lett., 2005, 7, 4111.
57. Freidinger, R.M.; Hinkle, J. S.; Perlow, D.S.; Arison, B.H. J. Org. Chem., 1983, 48, 77.
58. Aurelio, L.; Brownlee, R.T.C.; Hughes, A.B.; Sleebs, B.E. Aust. J. Chem., 2000, 53, 425.
59. Zhang, S.; Govender, T.; Norström, T.; Arvidsson, P.I. J. Org. Chem., 2005, 70, 6918.
60. Izzo, I.; Avallone, E.; Della Corte, L.; Maulucci, N.; De Riccardis. Tetrahedron Asymmetry, 2004, 14, 1181.
61. Muramatsu, H.; Mihara, H.; Kakutani, R.; Yasuda, M.; Ueda, M.; Kurihara, T.; Esaki, N. Tetrahedron Asymmetry, 2004, 15, 2841.
62. Tandom, V.K.; Yadav, D.B.; Singh, R.V.; Chaturvedi, A.K.; Shukla, P.S. Biorg. Med. Chem., 2005, 15, 5324.
63. Jiang, Y.; Tan, B.; Chen, Z.Z.; Liu, T.; Zhong, R.G.; Li, Y.M.; Stewart, D.J.; Zhao Y.F.; Jiang, H.L. Int. J. Quantum Chem., 2003, 94, 232.
64. Wu, L.Y.; Berkman, C.E. Tetrahedron Lett., 2005, 46, 5301.
65. O'Donnell, M.J.; Zhou, C.; Scott, W.L.; J. Am. Chem. Soc., 1996, 118, 6070.
66. Scott, W.L.; Zhou, C.; Fang, Z.; O'Donnell, M.J. Tetrahedron Lett., 1997, 38, 3695.
67. O'Donnell, M.J.; Lugar, C.W.; Pottorf, R.S.; Zhou, C. Tetrahedron Lett., 1997, 38, 7163.
68. Domínguez, E.; O'Donnell, M.J.; Scott, W.L. Tetrahedron Lett., 1998, 39, 2167.
69. O'Donnell, M.J.; Delgado, F.; Drew, M.D.; Pottorf, M.D.; Zhou, C.; Scott, W.L. Tetrahedron Lett., 1999, 40, 5831.
70. Scott, W.L.; Delgado, F.; Lobb, K.; Pottorf, M.D.; O'Donnell, M.J. Tetrahedron Lett., 2001, 42, 2073.
71. Scott W.L.; O'Donnell, M.J.; Delgado, F.; Alsina, J. J. Org. Chem., 2002, 67, 2960-2969.
72. O'Donnell, M.J.; Alsina, J.; Scott, W.L. Tetrahedron Lett., 2003, 44, 8403
73. Staszewska, A.; Stefanowicz, P.; Szewczuk, Z. Tetrahedron Lett., 2005, 46, 5525.
74. Paris, M.; Douat, C.; Heitz A.; Gibbons, W.; Martinez, J.; Fehrentz J.-A. Tetrahedron Lett., 1999, 40, 5179.
75. Kabalka, G.W.; Das, B.C.; Das, S. Tetrahedron Lett., 2001, 42, 7146.
76. Kabalka, G.W.; Wu, Z.Z.; Yao, M.-L.; Natarajan, N. Appl. Radiat. Isot., 2003, 61, 1111.
77. Kabalka, G.W.; Yao, M.-L. Synthesis, 2003, 2890.
78. Kabalka, G.W.; Yao, M.-L. J. Org. Chem., 2004, 69, 8280.
79. Kabalka, G.W.; Yao, M.-L.; Navarane, A. Tetrahedron Lett., 2005, 46, 4915.
80. Greenfield, S. J.; Gilbertson, S. R. Synthesis, 2001, 10, 2337-2340.
81. Davis, F.A.; Lee, S.; Yan, H.; Titus, D.D. Org. Lett., 2001, 3, 1757.
82. Birkofer, L.; Ritter, A. Angew. Chem., 1956, 68, 461.
83. Sieburth, S. McN.; Somers, J.J.; O'Hare, H.K. Tetrahedron, 1996, 52, 5669.
84. Liu, G.; Sieburth, S.M. Org. Lett., 2003, 5, 2677.
85. Degani V.; Heller, A. J. Am. Chem. Soc., 1988, 110, 2615.
86. Kira, M.; Matsubara, T.; Shinohara, H.; Sisido, M. Chem. Lett., 1997, 89.
87. Brosch, O.; Weyhermuller, T.; Metzler-Nolte, N. Eur. J. Inorg. Chem., 2000, 2, 323
88. Barišić, L.; Rapić, V.; Pritzkow, H.; Pavlović, G.; Nemet, I. J. Organomet. Chem., 2003, 682, 131.
89. Kuik, A.; Skoda-Földes, R.; Balogh, J.; Kollár, L. J. Organomet. Chem., 2005, 690, 3237.
90. Savage, D.; Malone, G.; Alley, S.R.; Gallagher, J.F.; Goel, A.; Kelly, P.N.; Bunz, H.M.; Kenny, P.T.M. J. Organomet. Chem., 2005, 691, 463.
91. Savage, D.; Neary, N.; Malone, G.; Alley, S.R.; Kenny, P.T.M. Inorg. Chem. Commun., 2005, 8, 429.
92. Ardá, A.; Jiménez, C.; Rodríguez, J. Tetrahedron Lett., 2004, 45, 3241.
93. Bravo, P.; Capelli, S.; Meille, S.V.; Seresini, P.; Volonterio, A.; Zanda, M. Tetrahedron Asymmetry, 1996, 7, 2321.
94. Jiang, Z.-X.; Liu, X.-P.; Qui, X.-L.; Qing, F.-L. J. Fluor. Chem., 2005, 126, 497.
95. Jiang, Z.-X.; Qing, F.-L. J. Org. Chem., 2004, 69, 5486.
96. Taylor, P.P.; Pantaleone, D.P.; Senkpeil, R.F. Fotheringham I.G. TIBTECH, 1998, 16, 412.
97. Bommarius, A.S.; Schwarm, M.; Drauz, K. J. Mol. Catal. B Enzym, 2001, 5, 1.
98. Altenbuchner, J.; Siemann-Herzberg, M. Curr. Opin. Biotechol., 2001, 12, 559-563.
99. Bommarius, A.S.; Drauz, K. Biorg. Med. Chem., 1994, 2, 617.
100. Lecointe, L.; Rolland-Fulcrand, V.; Roumestant, M.L.; Viallefont, P.; Martinez, J. Tetrahedron Asymmetry, 1998, 9, 1753.
101. Kise Jr., K.J.; Bowler, B.E. Tetrahedron Asymmetry, 1998, 9, 3319.
102. Zerkowski, J.A.; Hensley, L.M.; Abramowitz, D.M. Synlett, 2002, 29, 557.
103. Mann, E.; Kessler, H. Org. Lett., 2003, 5, 4567.
104. Kuijpers, B.H.M.; Groothuys, S.; Keereweer, A.B.R.; Quaedflieg, P.J.L.M.; Blaauw, R.H.; van Delft, F.L.; Rutjes, F.P.J.T. Org. Lett., 2004, 6, 3126.
105. Lane, J.W.; Halcomb, R.L. Tetrahedron, 2001, 57, 6531.
106. Enes, R.F.; Tomé, A.C.; Cavaleiro, J.A. Tetrahedron, 2005, 61, 1423.