α-Vinylic amino acids: occurrence, asymmetric synthesis, and biochemical mechanisms

Tetrahedron Asymmetry

Volumn 17, Issue 6, 2006, Pages 869-882

  Berkowitz, David B ^a   Charette, Bradley D ^a   Karukurichi, Kannan R ^a   McFadden, Jill M ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINO ACID; GLYCINE DERIVATIVE; NATURAL PRODUCT; PYRIDOXAL 5 PHOSPHATE; S METHYLMETHIONINE; VIGABATRIN; VINYL DERIVATIVE;

ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME INACTIVATION; ENZYME KINETICS; MICHAEL ADDITION; MOLECULAR MECHANICS; NONHUMAN; PRIORITY JOURNAL; REVIEW; X RAY CRYSTALLOGRAPHY;

EID: 33646098654     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.02.026     Document Type: Review

References (124)

1. Eliot A.C., and Kirsch J.F. Annu. Rev. Biochem. 73 (2004) 383-415
2. Berkowitz D.B., De la Salud-Bea R., and Jahng W.-J. Org. Lett. 6 (2004) 1821-1824
3. Berkowitz D.B., Chisowa E., and McFadden J.M. Tetrahedron 57 (2001) 6329-6343
4. Berkowitz D.B., McFadden J.M., and Sloss M.K. J. Org. Chem. 65 (2000) 2907-2918
5. Berkowitz D.B., McFadden J.M., Chisowa E., and Semerad C.L. J. Am. Chem. Soc. 122 (2000) 11031-11032
6. Berkowitz D.B., Jahng W.-J., and Pedersen M.L. Bioorg. Med. Chem. Lett. 6 (1996) 2151-2156
7. Pedersen M.L., and Berkowitz D.B. J. Org. Chem. 58 (1993) 6966-6975
8. Dardenne G., Casimir J., Marlier M., and Larsen P.O. Phytochemistry 13 (1974) 1897-1900
9. Posner B.I., and Flavin M. J. Biol. Chem. 247 (1972) 6402-6411
10. Flavin M., and Slaughter C. J. Biol. Chem. 235 (1960) 1112-1118
11. Kapke G., and Davis L. Biochem. Biophys. Res. Commun. 65 (1975) 765-769
12. Miles E.W. Biochem. Biophys. Res. Commun. 66 (1975) 94-102
13. Soper T.S., Manning J.M., Marcotte P.A., and Walsh C.T. J. Biol. Chem. 252 (1977) 1571-1575
14. Esaki N., Suzuki T., Tanaka H., Soda K., and Rando R.R. FEBS Lett. 84 (1977) 309-312
15. Johnston M., Raines R., Chang M., Esaki N., Soda K., and Walsh C. Biochemistry 20 (1981) 4325-4333
16. Walsh C., Pascal Jr. R.A., Johnston M., Raines R., Dikshit D., Krantz A., and Honma M. Biochemistry 20 (1981) 7509-7519
17. Rando R.R. Biochemistry 13 (1974) 3859-3863
18. Cornell N.W., Zuurendonk P.F., Kerich M.J., and Straight C.B. Biochem. J. 220 (1984) 707-716
19. Asada Y., Tanizawa K., Yonaha K., and Soda K. Agric. Biol. Chem. 52 (1988) 2873-2878
20. Marcotte P., and Walsh C. Biochemistry 15 (1976) 3070-3076
21. Zabriskie T.M., Klinge M., Szymanski C.M., Cheng H., and Vederas J.C. Arch. Insect Biochem. Physiol. 26 (1994) 27-48
22. Zabriskie T.M., Cheng H., and Vederas J.C. J. Am. Chem. Soc. 114 (1992) 2270-2272
23. Zheng L., White R.H., Cash V.L., and Dean D.R. Biochemistry 33 (1994) 4714-4720
24. Capitani G., Tschopp M., Eliot A.C., Kirsch J.F., and Grütter M.G. FEBS Lett. 579 (2005) 2458-2462
25. Ko S., Eliot A.C., and Kirsch J.F. Arch. Biochem. Biophys. 421 (2004) 85-90
26. McCarthy D.L., Capitani G., Feng L., Gruetter M.G., and Kirsch J.F. Biochemistry 40 (2001) 12276-12784
27. Feng L., and Kirsch J.F. Biochemistry 39 (2000) 2436-2444
28. Satoh S., and Yang S.F. Arch. Biochem. Biophys. 271 (1989) 107-112
29. Culvenor C.C.J., Edgar J.A., Mackay M.F., Gorst-Allman C.P., Marasas W.F.O., Steyn P.S., Vleggaar R., and Wessels P.L. Tetrahedron 45 (1989) 2351-2372
30. Mackay M.F., Van Donkelaar A., and Culvenor C.C.J. J. Chem. Soc., Chem. Commun. (1986) 1219-1221
31. Levenberg B. J. Biol. Chem. 243 (1968) 6009-6013
32. Campos L., Marlier M., Dardenne G., and Casimir J. Phytochemistry (Elsevier) 22 (1983) 2507-2508
33. Vervier R., and Casimir J. Phytochemistry (Elsevier) 9 (1970) 2059-2060
34. Scannell J.P., Pruess D.L., Demny T.C., Sello L.H., Williams T., and Stempel A. J. Antibiot. 25 (1972) 122-127
35. Sahm U., Knobloch G., and Wagner F. J. Antibiot. 26 (1973) 389-390
36. Miles E.W. Enzyme-Act. Irreversible Inhibitors, Proc. Int. Symp. (1978) 73-85
37. Rando R.R. Nature 250 (1974) 586-587
38. Rando R.R., Relyea N., and Cheng L. J. Biol. Chem. 251 (1976) 3306-3312
39. Dashman T. Life Sci. 27 (1980) 1415-1522
40. Dashman T., and Kamm J.J. Life Sci. 24 (1979) 185-192
41. Gonzalez B., Pajares M.A., Hermoso J.A., Guillerm D., Guillerm G., and Sanz-Aparicio J. J. Mol. Biol. 331 (2003) 407-416
42. Gonzalez B., Pajares M.A., Hermoso J.A., Alvarez L., Garrido F., Sufrin J.R., and Sanz-Aparicio J. J. Mol. Biol. 300 (2000) 363-375
43. Pruess D.L., Scannell J.P., Kellett M., Ax H.A., Janecek J., Williams T.H., Stempel A., and Berger J. J. Antibiot. 27 (1974) 229-233
44. Clausen T., Huber R., Messerschmidt A., Pohlenz H.D., and Laber B. Biochemistry 36 (1997) 12633-12643
45. Steegborn C., Clausen T., Sondermann P., Jacob U., Worbs M., Marinkovic S., Huber R., and Wahl M.C. J. Biol. Chem. 274 (1999) 12675-12684
46. Krupka H.I., Huber R., Holt S.C., and Clausen T. EMBO J. 19 (2000) 3168-3178
47. Icekson I., and Apelbaum A. Biochem. Biophys. Res. Commun. 113 (1983) 586-591
48. Huai Q., Xia Y., Chen Y., Callahan B., Li N., and Ke H. J. Biol. Chem. 276 (2001) 38210-38216
49. Capitani G., McCarthy D.L., Gut H., Grutter M.G., and Kirsch J.F. J. Biol. Chem. 277 (2002) 49735-49742
50. Owens L.D., Guggenheim S., and Hilton J.L. Biochim. Biophys. Acta, Gen. Subj. 158 (1968) 219-225
51. Owens L.D., Thompson J.F., Pitcher R.G., and Williams T. J. Chem. Soc., Chem. Commun. (1972) 714
52. Yasuta T., Okazaki S., Mitsui H., Yuhashi K.-I., Ezura H., and Minamisawa K. Appl. Environ. Microbiol. 67 (2001) 4999-5009
53. Mitchell R.E., Frey E.J., and Benn M.H. Phytochemistry 25 (1986) 2711-2715
54. Giovanelli J., Owens L.D., and Mudd S.H. Biochim. Biophys. Acta 227 (1971) 671-684
55. Minamisawa K., Fukai K., and Asami T. J. Bacteriol. 172 (1990) 4505-4509
56. Yasuta T., Satoh S., and Minamisawa K. Appl. Environ. Microbiol. 65 (1999) 849-852
57. Ma W., Penrose Donna M., and Glick Bernard R. Can. J. Microbiol. 48 (2002) 947-954
58. Rapp C., Jung G., Kugler M., and Loeffler W. Liebigs Ann. Chem. (1988) 655-661
59. Fredenhagen A., Angst C., and Peter H.H. J. Antibiot. 48 (1995) 1043-1045
60. Park B.K., Hirota A., and Sakai H. Agric. Biol. Chem. 40 (1976) 1905-1906
61. Steegborn C., Laber B., Messerschmidt A., Huber R., and Clausen T. J. Mol. Biol. 311 (2001) 789-801
62. Laber B., Lindell S.D., and Pohlenz H.D. Arch. Microbiol. 161 (1994) 400-403
63. Murakami N., Furukawa J., Okuda S., and Hatanaka S. Phytochemistry 24 (1985) 2291-2294
64. Murakami N., and Hatanaka S. Phytochemistry 22 (1983) 2735-2737
65. Timmermans M., Randoux T., Daloze D., Braekman J.C., Pasteels J.M., and Lesage L. Biochem. Syst. Ecol. 20 (1992) 343-349
66. Plasman V., Plehiers M., Braekman J.C., Daloze D., De Biseau J.C., and Pasteels J.M. Chemoecology 11 (2001) 107-112
67. Aoyagi Y., Takasaki S., Fujihara S., Kasuga A., and Sugahara T. Phytochemistry 46 (1997) 1095-1096
68. Matsuda H., Okino T., Haraguchi R., Murakami M., and Yamaguchi K. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 35 (1993) 654-661
69. Matsuda H., Okino T., Murakami M., and Yamaguchi K. J. Org. Chem. 61 (1996) 8648-8650
70. Coleman J.E., and Wright J.L. J. Nat. Prod. 64 (2001) 668-670
71. Doyle R.R., and Levenberg B. Biochemistry 7 (1968) 2457-2462
72. Chaiet L., Arison B.H., Monaghan R.L., Springer J.P., Smith J.L., and Zimmerman S.B. J. Antibiot. 37 (1984) 207-210
73. Rajesh S., Ami E.i., Kotake T., Tsukamoto H., Kimura T., Hayashi Y., and Kiso Y. Pept. Sci. 39 (2003) 151-152
74. Paleo M.R., Aurrecoechea N., Jung K.-Y., and Rapoport H. J. Org. Chem. 68 (2003) 130-138
75. Nolen E.G., Kurish A.J., Wong K.A., and Orlando M.D. Tetrahedron Lett. 44 (2003) 2449-2453
76. Rajesh S., Ami E.i., Kotake T., Kimura T., Hayashi Y., and Kiso Y. Bioorg. Med. Chem. Lett. 12 (2002) 3615-3617
77. Collier P.N., Campbell A.D., Patel I., and Taylor R.J.K. Tetrahedron 58 (2002) 6117-6125
78. Gao Y., Lane-Bell P., and Vederas J.C. J. Org. Chem. 63 (1998) 2133-2143
79. Huwe C.M., and Blechert S. Synthesis (1997) 61-67
80. Yoo S.e., Lee S.H., Jeong N., and Cho I. Tetrahedron Lett. 34 (1993) 3435-3438
81. Zeiss H.J. Tetrahedron 48 (1992) 8263-8270
82. Crisp G.T., and Glink P.T. Tetrahedron 48 (1992) 3541-3556
83. Zahn I., Polborn K., Wagner B., and Beck W. Chem. Ber. 124 (1991) 1065-1073
84. Krol W.J., Mao S.S., Steele D.L., and Townsend C.A. J. Org. Chem. 56 (1991) 728-731
85. Meffre P., Vo Quang L., Vo Quang Y., and Le Goffic F. Tetrahedron Lett. 31 (1990) 2291-2294
86. Mzengeza S., and Whitney R.A. J. Org. Chem. 53 (1988) 4074-4081
87. Wityak J., Gould S.J., Hein S.J., and Keszler D.A. J. Org. Chem. 52 (1987) 2179-2183
88. Mzengeza S., Yang C.M., and Whitney R.A. J. Am. Chem. Soc. 109 (1987) 276-277
89. Fushiya S., Chiba H., Otsubo A., and Nozoe S. Chem. Lett. (1987) 2229-2232
90. Cardani S., Prati L., and Tinti O. Synthesis (1986) 1032-1035
91. Afzali-Ardakani A., and Rapoport H. J. Org. Chem. 45 (1980) 4817-4820
92. Griesbeck A.G., and Heckroth H. Photochem. Photobiol. Sci. 2 (2003) 1130-1133
93. Griesbeck A.G., and Hirt J. Liebigs Ann. Chem. (1995) 1957-1961
94. Berkowitz D.B., and Smith M.K. Synthesis (1996) 39-41
95. Pellicciari R., Natalini B., and Marinozzi M. Synth. Commun. 18 (1988) 1715-1721
96. Zhang W., Luo S., Fang F., Chen Q., Hu H., Jia X., and Zhai H. J. Am. Chem. Soc. 127 (2005) 18-19
97. Feldman K.S., Perkins A.L., and Masters K.M. J. Org. Chem. 69 (2004) 7928-7932
98. Grieco P.A., Gilman S., and Nishizawa M. J. Org. Chem. 41 (1976) 1485-1486
99. Hanessian S., and Sahoo S.P. Tetrahedron Lett. 25 (1984) 1425-1428
100. Barton D.H.R., Crich D., Herve Y., Potier P., and Thierry J. Tetrahedron 41 (1985) 4347-4357
101. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., and Galvez J.A. Synthesis (1997) 747-749
102. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., Diez R., and Galvez J.A. Eur. J. Org. Chem. (2003) 2268-2275
103. Rose N.G.W., Blaskovich M.A., Wong A., and Lajoie G.A. Tetrahedron 57 (2001) 1497-1507
104. Beaulieu P.L., Duceppe J.S., and Johnson C. J. Org. Chem. 56 (1991) 4196-4204
105. Friis P., Helboe P., and Larsen P.O. Acta Chem. Scand., B, Org. Chem. Biochem. 28 (1974) 317-321
106. Hallinan K.O., Crout D.H.G., and Errington W. J. Chem. Soc., Perkin Trans. 1 (1994) 3537-3543
107. Schöllkopf U., Nozulak J., and Groth U. Tetrahedron 40 (1984) 1409-1417
108. Hudrlik P.F., and Kulkarni A.K. J. Am. Chem. Soc. 103 (1981) 6251-6253
109. Trost B.M., and Bunt R.C. J. Am. Chem. Soc. 122 (2000) 5968-5976
110. Trost B.M. Pure Appl. Chem. 68 (1996) 779-784
111. Trost B.M., and Bunt R.C. Angew. Chem., Int. Ed. 35 (1996) 99-102
112. Berkowitz D.B., Bose M., and Choi S. Angew. Chem., Int. Ed. 41 (2002) 1603-1607
113. Berkowitz D.B., Shen W., and Maiti G. Tetrahedron: Asymmetry 15 (2004) 2845-2851
114. Berkowitz D.B., and Maiti G. Org. Lett. 6 (2004) 2661-2664
115. Keith D.D., Tortora J.A., and Yang R. J. Org. Chem. 43 (1978) 3711-3713
116. Alks V., and Sufrin J.R. Tetrahedron Lett. 31 (1990) 5257-5260
117. Keith D.D., Tortora J.A., Ineichen K., and Leimgruber W. Tetrahedron 31 (1975) 2633-2636
118. Czapinski P., Blaszczyk B., and Czuczwar S.J. Curr. Top. Med. Chem. 5 (2005) 3-14
119. Nanavati S.M., and Silverman R.B. J. Am. Chem. Soc. 113 (1991) 9341-9349
120. De Biase D., Barra D., Bossa F., Pucci P., and John R.A. J. Biol. Chem. 266 (1991) 20056-20061
121. Storici P., De Biase D., Bossa F., Bruno S., Mozzarelli A., Peneff C., Silverman R.B., and Schirmer T. J. Biol. Chem. 279 (2004) 363-373
122. Brodie J.D., Figueroa E., Laska E.M., and Dewey S.L. Synapse 55 (2005) 122-125
123. Gerasimov M.R., and Dewey S.L. Drug Dev. Res. 59 (2003) 240-248
124. Brodie J.D., Figueroa E., and Dewey S.L. Synapse 50 (2003) 261-265