7.11 Reduction: Enantioselective Bioreduction of C-C Double Bonds

Comprehensive Chirality

Volumn 7, Issue , 2012, Pages 216-255

  Toogood, H S ^a   Mansell, D ^a   Gardiner, J M ^a   Scrutton, N S ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Alkene reduction; Baker's yeast; Biocatalysis; Coenzyme recycling; Old yellow enzyme family

Indexed keywords

EID: 84895740421     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-095167-6.00713-8     Document Type: Chapter

References (232)

1. Stuermer R., Hauer B., Hall M., Faber K. Curr. Opin. Chem. Biol. 2007, 11(2):203-213.
2. Knowles W.S. Acc. Chem. Res. 1983, 16(39):106-112.
3. Tuttle J.B., Ouellet G.G., MacMillan D.W.C. J. Am. Chem. Soc. 2006, 128(39):12662-12663.
4. Turner N. Trend Biotechnol. 2003, 21(11):474-478.
5. Chirumamilla R., Muralidhar R., Marchant R., Nigam P. Mol. Cell. Biochem. 2001, 224(1-2):159-168.
6. Panke S., Held M., Wubbolts M. Curr. Opin. Biotechnol. 2004, 15(4):272-279.
7. Reetz M.T. Asymmetric Organic Synthesis with Enzymes 2008, 21-63. Wiley-VCH, Weinheim, Chapter 2. V. Gotor, I. Alfonso, E. Garcia-Urdiales (Eds.).
8. Straathof A.J.J., Panke S., Schmid A. Curr. Opin. Biotechnol. 2002, 13(6):548-556.
9. Buque E., Chin-Joe I., Straathof A., Jongejan J., Heijnen J. Enzyme Microb. Technol. 2002, 31(5):656-664.
10. Bommarius A.S. Biocatalysis Fundamental and Applications 2004, Wiley-VCH, Weinheim, pp 2-578.
11. Christmann M., Brase S. Asymmetric Synthesis the Essentials 2007, Wiley-VCH, Weinheim.
12. Enders D., Jaeger K.-E. Asymmetric Synthesis with Chemical and Biological Methods 2007, Wiley-VCH, Weinheim.
13. Guisan J.M., Fernandez-Lafuente R., Wilson L., Mateo C. Enzyme Biocatalysis Principles and Applications 2008, 324-333. Springer, Berlin, Chapter 6.4. A. Illanes (Ed.).
14. Grunwald P. Biocatalysis Biochemical Fundamentals and Applications 2009, Imperial College Press, Singapore.
15. Helgueira Andrade L., Nakamura K. Handbook of Green Chemistry: Green Catalysis 2009, Vol. 3:151-170. Wiley-VCH, Weinheim, Chapter 6.
16. Bommarius A., Polizzi K. Chem. Eng. Sci. 2006, 61(3):1004-1016.
17. Gunther H., Simon H. Biocatal. Biotransform. 1995, 12(1):1-26.
18. Simon H., Bader J., Gunther H., Neumann S., Thanos J. Angew. Chem., Int. Ed. 1985, 24(7):539-553.
19. Toogood H.S., Gardiner J.M., Scrutton N.S. ChemCatChem 2010, 2(8):892-914.
20. Williams R., Bruce N. Microbiology 2002, 148(6):1607-1614.
21. Stueckler C., Hall M., Ehammer H., et al. Org. Lett. 2007, 9(26):5409-5411.
22. Hirata T., Shimoda K., Gondai T. Chem. Lett. 2000, 29(8):850-851.
23. Davies E.T., Stephens G.M. Appl. Environ. Microbiol. 1996, 46(5-6):615-618.
24. Eck R., Simon H. Tetrahedron 1994, 50(48):13631-13640.
25. Simon H., Rambeck B., Hashimoto H., et al. Angew. Chem., Int. Ed. 1974, 13(9):608-609.
26. Angermaier L., Bader J., Simon H. Hoppe-Seyler's Z. Physiol. Chem. 1981, 362(1):33-38.
27. Fauve A., Renard M., Veschambre H. J. Org. Chem. 1987, 52(22):4893-4897.
28. Fronza G., Fuganti C., Grasselli P., et al. J. Chem. Soc. Perkin Trans. 1 1994, 20:2927-2930.
29. Fryszkowska A., Fisher K., Gardiner J., Stephens G. J. Org. Chem. 2008, 73(11):4295-4298.
30. Fuganti C., Chiringhell D. J. Chem. Soc. Chem. Commun. 1975, 729:846-847.
31. Speicher A., Roeser H., Heisel R. J. Mol. Catal. B: Enzym. 2003, 22(1-2):71-77.
32. Goretti M., Ponzoni C., Caselli E., et al. Enzyme Microb. Technol. 2009, 45(6-7):463-468.
33. Sakai K., Nakazawa A., Kondo K., Ohta H. Agric. Biol. Chem. Tokyo 1985, 49(8):2331-2335.
34. Hori N., Hieda T., Mikami Y. Agric. Biol. Chem. 1984, 48(1):123-129.
35. McAnda A., Roberts K., Smallridge A., Ten A., Trewhella M. J. Chem. Soc. Perkin Trans. 1 1998, (3):501-504.
36. Nakamura K., Kondo S., Kawai Y., Ohno A. Tetrahedron Lett. 1991, 32(48):7075-7078.
37. Noma Y., Okajima Y., Takahashi H., Asakawa Y. Phytochemistry 1991, 30(9):2969-2972.
38. Noma Y., Takahashi H., Asakawa Y. Phytochemistry 1991, 30(4):1147-1151.
39. Hall M., Hauer B., Stuermer R., Kroutil W., Faber K. Tetrahedron: Asymmetry 2006, 17(21):3058-3062.
40. Matsumoto S., Kawabata Y., Takahashi J., Fujita Y., Hatanaka M. Chem. Lett. 1998, 27(4):283-284.
41. Bougioukou D.J., Walton A.Z., Stewart J.D. Chem. Commun. 2010, 46(45):8558-8560.
42. Fryszkowska A., Toogood H., Sakuma M., et al. Adv. Synth. Catal. 2009, 351(17):2976-2990.
43. Hall M., Stueckler C., Ehammer H., et al. Adv. Synth. Catal. 2008, 350(3):411-418.
44. Kataoka M., Kotaka A., Hasegawa A., et al. Biosci. Biotechnol. Biochem. 2002, 66(12):2651-2657.
45. Toogood H., Fryszkowska A., Hulley M.E., et al. ChemBioChem 2011, 12(5):738-749.
46. Hall M., Stueckler C., Hauer B., et al. Eur. J. Org. Chem., 2008, 2008(9):1511-1516.
47. Hall M., Stueckler C., Kroutil W., Macheroux P., Faber K. Angew. Chem., Int. Ed. 2007, 46(21):3934-3937.
48. Swiderska M., Stewart J. J. Mol. Catal. B: Enzym. 2006, 42(1-2):52-54.
49. Swiderska M.A., Stewart J.D. Org. Lett. 2006, 8(26):6131-6133.
50. Toogood H.S., Fryszkowska A., Hare V., et al. Adv. Synth. Catal. 2008, 350(17):2789-2803.
51. Beynon E.R., Symons Z.C., Jackson R.G., et al. Plant Physiol. 2009, 151(1):253-261.
52. Binks P., French C., Nicklin S., Bruce N. Appl. Environ. Microbiol. 1996, 62(4):1214-1219.
53. French C., Rosser S., Davies G., Nicklin S., Bruce N. Nat. Biotechnol. 1999, 17(5):491-494.
54. Vanek T., Gerth A., Vakrikova Z., et al. Advanced Science and Technology for Biological Decontamination of Sites Affected by Chemical and Radiological Nuclear Agents 2007, Springer, The Netherlands, pp 209-225.
55. Adalbjornsson B., Toogood H.S., Fryszkowska A., et al. ChemBioChem 2010, 11(2):197-207.
56. Kitzing K., Fitzpatrick T., Wilken C., et al. J. Biol. Chem. 2005, 280(30):27904-27913.
57. Snape J., Walkley N., Morby A., Nicklin S., White G. J. Bacteriol. 1997, 179(24):7796-7802.
58. Stueckler C., Winkler C.K., Bonnekessel M., Faber K. Adv. Synth. Catal. 2010, 352(14-15):2663-2666.
59. Mueller N., Stueckler C., Hauer B., et al. Adv. Synth. Catal. 2010, 352(2-3):387-394.
60. Chaparro-Riggers J., Rogers T., Vazquez-Figueroa E., Polizzi K., Bommarius A. Adv. Synth. Catal. 2007, 349(8-9):1521-1531.
61. Fitzpatrick T., Amrhein N., Macheroux P. J. Biol. Chem. 2003, 278(22):19891-19897.
62. Brige A., van den Hemel D., Carpentier W., de Smet L., van Beeumen J.J. Biochem. J. 2006, 394(1):335-344.
63. Sobajima H., Takeda M., Sugimori M., et al. Planta 2003, 216(4):692-698.
64. Hirata T., Matsushima A., Sato Y., et al. J. Mol. Catal. B: Enzym. 2009, 59(1-3):158-162.
65. Matsushima A., Sato Y., Otsuka M., et al. Bioorg. Chem. 2008, 36(1-3):23-28.
66. Rohdich F., Wiese A., Feicht R., Simon H., Bacher A. J. Biol. Chem. 2001, 276(8):5779-5787.
67. Winkler C., Stueckler C., Mueller N., Pressnitz D., Faber K. Eur. J. Org. Chem. 2010, 2010(33):6354-6358.
68. Schuhle K., Jahn M., Ghisla S., Fuchs G. J. Bacteriol. 2001, 183(18):5268-5278.
69. Bougioukou D.J., Kille S., Taglieber A., Reetz M. Adv. Synth. Catal. 2009, 351(18):3287-3305.
70. Taglieber A., Schulz F., Hollmann F., Rusek M., Reetz M. ChemBioChem 2008, 9(4):565-572.
71. Buhler M., Giesel H., Tischer W., Simon H. FEBS Lett. 1980, 109(2):244-246.
72. Hetzel M., Brock M., Selmer T., et al. Eur. J. Biochem. 2003, 270(5):902-910.
73. Buhler M., Simon H. Hoppe-Seyler's Z. Physiol. Chem. 1982, 363(1):609-662.
74. French C., Nicklin S., Bruce N. J. Bacteriol. 1996, 178(22):6623-6627.
75. Khan H., Barna T., Bruce N.C., et al. FEBS J. 2005, 272:4660-4671.
76. Khan H., Barna T., Harris R., et al. J. Biol. Chem. 2004, 279(29):30563-30572.
77. Khan H., Harris R., Barna T., et al. J. Biol. Chem. 2002, 277(24):21906-21912.
78. Miseviciene L., Anusevicius Z., Sarlauskas J., et al. Acta Biochim. Pol. 2007, 54(2):379-385.
79. Hulley M.E., Toogood H.S., Fryszkowska A., et al. ChemBioChem 2010, 11(17):2433-2447.
80. Williams R., Rathbone D., Scrutton N., Bruce N. Appl. Environ. Microbiol. 2004, 70(6):3566-3574.
81. Schweiger P., Gross H., Wesener S., Deppenmeier U. Appl. Microbiol. Biotechnol. 2008, 80(6):995-1006.
82. Yin B., Yang X., Wei G., Ma Y., Wei D. Mol. Biotechnol. 2008, 38(3):241-245.
83. Shimada Y., Yasuda S., Takahashi M., et al. Appl. Environ. Microbiol. 2010, 76(17):5892-5901.
84. Blehert D., Fox B., Chambliss G. J. Bacteriol. 1999, 181(20):6254-6263.
85. Barna T., Messiha H., Petosa C., et al. J. Biol. Chem. 2002, 277(34):30976-30983.
86. Messiha H.L., Munro A., Bruce N., Barsukov I., Scrutton N. J. Biol. Chem. 2005, 280(11):10695-10709.
87. van Dillewijn P., Wittich R., Caballero A., Ramos J. Appl. Environ. Microbiol. 2008, 74(21):6703-6708.
88. Griese J., Jakob R.P., Schwarzinger S., Dobbek H. J. Mol. Biol. 2006, 361(1):140-152.
89. Spiegelhauer O., Dickert F., Mende S., et al. Biochemistry 2009, 48(48):11412-11420.
90. Rohde B., Schmid R., Ullrich M. J. Bacteriol. 1999, 181(3):814-822.
91. Yanto Y., Hall M., Bommarius A.S. Org. Biomol. Chem. 2010, 8(8):1826-1832.
92. Wardrope C., Mowat C., Walkinshaw M., Reid G., Chapman S. FEBS Lett. 2006, 580(6):1677-1680.
93. Liu H., Wallace K., Reynolds K. J. Am. Chem. Soc. 1997, 119(13):2973-2979.
94. Reynolds K. J. Nat. Prod. 1993, 56(2):175-185.
95. Opperman D.J., Piater L.A., van Heerden E. J. Bacteriol. 2008, 190(8):3076-3082.
96. Opperman D.J., Sewell B.T., Litthauer D., et al. Biochem. Biophys. Res. Commun. 2010, 393(3):426-431.
97. Muller A., Hauer B., Rosche B. Biotechnol. Bioeng. 2007, 98(1):22-29.
98. Mano J., Belles-Boix E., Babiychuk E., et al. Plant Physiol. 2005, 139(4):1773-1783.
99. Costa C., Arruda P., Benedetti C. Plant Mol. Biol. 2000, 44(1):61-71.
100. Schaller F., Biesgen C., Müssig C., Altmann T., Weiler E. Planta 2000, 210(6):979-984.
101. Burda E., Krausser M., Fischer G., et al. Adv. Synth. Catal. 2009, 351(17):2787-2790.
102. Herl V., Fischer G., Reva V.A., et al. Biochimie 2009, 91(4):517-525.
103. Zhang Y., Teoh K.H., Reed D.W., Covello P.S. Botany 2009, 87(6):643-649.
104. Schaller F., Hennig P., Weiler E. Plant Physiol. 1998, 118(4):1345-1351.
105. Herl V., Fischer G., Mueller-Uri F., Kreis W. Phytochemistry 2006, 67(14):1554.
106. Shimoda K., Kubota N., Hirata T., Kondo Y., Hamada H. Tetrahedron Lett. 2007, 48(8):1345-1347.
107. Shimoda K., Kubota N. Tetrahedron: Asymmetry 2004, 15(24):3827-3829.
108. Ringer K.L., Davis E.M., Croteau R. Plant Physiol. 2005, 137(3):863-872.
109. Hirata T., Tamura Y., Yokobatake N., Shimoda K., Ashida Y. Phytochemistry 2000, 55(4):297-303.
110. Shimoda K., Kubota N., Hamada H. Tetrahedron: Asymmetry 2004, 15(15):2443-2446.
111. Shimoda K., Izumi S., Hirata T. Bull. Chem. Soc. Jpn. 2002, 75(4):813-816.
112. Hirata T., Tang Y., Okano K., Suga T. Phytochemistry 1989, 28(12):3331-3333.
113. Shimoda K., Ito D., Izumi S., Hirata T. J. Chem. Soc. Perkin Trans. 1 1996, (4):355-358.
114. Kasahara H., Jiao Y., Bedgar D.L., et al. Phytochemistry 2006, 67(16):1765-1780.
115. Strassner J., Furholz A., Macheroux P., Amrhein N., Schaller A. J. Biol. Chem. 1999, 274(49):35067-35073.
116. Stueckler C., Mueller N.J., Winkler C.K., et al. Dalton Trans. 2010, 39(36):8472-8476.
117. Cheng J.Z., Coyle C.M., Panaccione D.G., O'Connor S.E. J. Am. Chem. Soc. 2010, 132(6):1776-1777.
118. Cheng J.Z., Coyle C.M., Panaccione D.G., O'Connor S.E. J. Am. Chem. Soc. 2010, 132(37):12835-12837.
119. Kawai Y., Inaba Y., Hayashi M., Tokitoh N. Tetrahedron Lett. 2001, 42(19):3367-3368.
120. Kawai Y., Hayashi M., Inaba Y., Saitou K., Ohno A. Tetrahedron Lett. 1998, 39(29):5225-5228.
121. Buckman J., Miller S. Biochemistry 1998, 37(40):14326-14336.
122. Mizugaki M., Nakazawa M., Yamamoto H., Yamanaka H. J. Biochem. Tokyo 1989, 105(1):782-784.
123. Kataoka M., Kotaka A., Thiwthong R., et al. J. Biotechnol. 2004, 114(1-2):1-9.
124. Shaw P.D. Biochemistry 1967, 6(7):2253-2260.
125. Muller A., Sturmer R., Hauer B., Rosche B. Angew. Chem., Int. Ed. 2007, 46(18):3316-3318.
126. Niino Y., Chakraborty S., Brown B., Massey V. J. Biol. Chem. 1995, 270(5):1983-1991.
127. Wada M., Yoshizumi A., Noda Y., et al. Appl. Environ. Microbiol. 2003, 69(2):933-937.
128. Brown B., Deng Z., Karplus P., Massey V. J. Biol. Chem. 1998, 273(49):32753-32762.
129. Stott K., Saito K., Thiele D.J., Massey V. J. Biol. Chem. 1993, 268(9):6097-6106.
130. Kohli R., Massey V. J. Biol. Chem. 1998, 273(49):32763-32770.
131. Meah Y., Massey V. Proc. Natl. Acad. Sci. USA 2000, 97(20):10733-10738.
132. Padhi S., Bougioukou D., Stewart J. J. Am. Chem. Soc. 2009, 131(9):3271-3280.
133. Vaz A., Chakraborty S., Massey V. Biochemistry 1995, 34(13):4246-4256.
134. Shimoda K., Hirata T. J. Mol. Catal. B: Enzym. 2000, 8(4-6):255-264.
135. Shimoda K., Hirata T., Noma Y. Phytochemistry 1998, 49(1):49-53.
136. Porte S., Moeini A., Reche I., et al. Cell. Mol. Life Sci. 2010, 68(6):1065-1077.
137. Chu X., Yu W., Chen G., Li D. Protein Expression Purif. 2003, 31(2):292-297.
138. Bougioukou D.J., Stewart J.D. J. Am. Chem. Soc. 2008, 130(24):7655-7658.
139. Fillgrove K., Anderson V. Biochemistry 2000, 39(23):7001-7011.
140. Kosjek B., Fleitz F.J., Dormer P.G., Kuethe J.T., Devine P.N. Tetrahedron: Asymmetry 2008, 19(12):1403-1406.
141. Mano J., Torii Y., Hayashi S., et al. Plant Cell Physiol. 2002, 43(12):1445-1455.
142. Schaller F., Weiler E. J. Biol. Chem. 1997, 272(44):28066-28072.
143. Shimoda K., Kubota N., Hamada H., Kaji M., Hirata T. Tetrahedron: Asymmetry 2004, 15(11):1677-1679.
144. Bader J. Arch. Microbiol. 1980, 127(3):279-287.
145. Simon H. Pure Appl. Chem. 1992, 64(8):1181-1186.
146. Ageishi K., Endo T., Okawara M. J. Polym. Sci. 1983, 21:175-181.
147. Grau M.M., van der Toorn J.C., Otten L.G., et al. Adv. Synth. Catal. 2009, 351(18):3279-3286.
148. Stueckler C., Reiter T.C., Baudendistel N., Faber K. Tetrahedron 2010, 66(3):663-667.
149. Abramovitz A., Massey V. J. Biol. Chem. 1976, 251(17):5327-5336.
150. Mohr S., Fisher K., Scrutton N.S., Goddard N.J., Fielden P.R. Lab. Chip 2010, 10:1929-1936.
151. Kirk R.E., Othmer D.F. Kirk-Othmer Encyclopedia of Chemical Technology 2005, Wiley-VCH, New York.
152. Kergomard A., Renard M.F., Veschambre H. J. Org. Chem. 1982, 47(5):792-798.
153. Bostmembrun-Desrut M., Kergomard A., Renard M., Veschambre H. Agric. Biol. Chem. Tokyo 1983, 47(9):1997-2000.
154. Desrut M., Kergomard A., Renard M., Veschambre H. Biochem. Biophys. Res. Commun. 1983, 110(3):908-912.
155. Kergomard A., Renard M., Veschambre H. Tetrahedron Lett. 1978, 52(52):5197-5200.
156. Kergomard A., Renard M., Veschambre H. Agric. Biol. Chem. Tokyo 1982, 46(1):97-99.
157. Kergomard A., Renard M., Veschambre H. Agric. Biol. Chem. Tokyo 1985, 49(5):1497-1499.
158. Kergomard A., Renard M., Veschambre H., Courtois D., Petiard V. Phytochemistry 1988, 27(2):407-409.
159. Kergomard A., Renard M.F., Veschambre H., Groliere C.A., Dupyblanc J. Agric. Biol. Chem. Tokyo 1986, 50(2):487-489.
160. Basran J., Harris R., Sutcliffe M., Scrutton N. J. Biol. Chem. 2003, 278(45):43973-43982.
161. French C., Bruce N. Biochem. J. 1994, 301(Pt 1):97-103.
162. Madani N., Malloy P., Rodriguez-Pombo P., Krishnan A., Feldman D. Proc. Natl. Acad. Sci. USA 1994, 91(3):922-926.
163. Yanto Y., Yu H.-H., Hall M., Bommarius A.S. Chem. Commun. 2010, 46(46):8809.
164. Fogliato G., Fronza G., Fuganti C., et al. Tetrahedron 1995, 51(37):10231-10240.
165. Chin-Joe I., Straathof A., Pronk J., Jongejan J., Heijnen J. Biotechnol. Bioeng. 2001, 75(1):29-38.
166. Kawai Y., Hayashi M., Tokitoh N. Tetrahedron: Asymmetry 2001, 12(21):3007-3013.
167. Aleu J., Fronza G., Fuganti C., Perozzo V., Serra S. Tetrahedron: Asymmetry 1998, 9(9):1589.
168. Kawai Y., Saitou K., Hida K., Ohno A. Tetrahedron: Asymmetry 1995, 6(9):2143-2144.
169. Fuganti C., Minut J., Fantoni G., Servi S. J. Mol. Catal. B: Enzym. 1998, 4(1-2):47-52.
170. Zagozda M., Plenkiewicz J. Tetrahedron: Asymmetry 2006, 17(13):1958-1962.
171. Dumanski P.G., Florey P., Knettig M., Smallridge A., Trewhella M. J. Mol. Catal. B: Enzym. 2001, 11:905-908.
172. Kitazume T., Ishikawa N. Chem. Lett. 1984, 13(4):587-590.
173. Leuenberger H.G.W., Boguth W., Widmer E., Zell R. Helv. Chim. Acta 1976, 59:1832-1849.
174. Yamazaki Y., Hayashi Y., Hori N., Mikami Y. Agric. Biol. Chem. 1988, 52(11):2919-2920.
175. Tang Y., Suga T. Phytochemistry 1994, 37(3):737-740.
176. McAuley C., McShane T. Arch. Dis. Child.: Edu. Prac. Edu. 2010, 10.1136/adc.2010.199299.
177. Seijas J.A., Vazquez-Tato M.P., Martinez M.M., Nunez-Corredoira G.J. J. Chem. Res. Synop. 1999, 420-421.
178. Hirata T., Takarada A., Matsushima A., Konodo Y., Hamada H. Tetrahedron: Asymmetry 2004, 15(1):15-16.
179. Fronza G., Fuganti C., Grasselli P., et al. Tetrahedron Lett. 1993, 34(40):6467-6470.
180. Takabe K., Hiyoshi H., Sawada H., et al. Tetrahedron: Asymmetry 1992, 3(11):1399-1400.
181. Fronza G., Fuganti C., Mendozza M., et al. Pure Appl. Chem. 1996, 68(11):2065-2071.
182. Fronza G., Fuganti C., Grasselli P., Barbeni M. Tetrahedron Lett. 1992, 33(42):6375-6378.
183. Fuganti C., Pedrocchi-Fantoni G., Sarra A., Servi S. Tetrahedron: Asymmetry 1994, 5(7):1135-1138.
184. van der Schaft P., ter Burg N., van den Bosch S., Cohen A. Appl. Microbiol. Biotechnol. 1992, 36(6):712-716.
185. Bostmembrun-Desrut M., Dauphin G., Kergomard A., Renard M., Veschambre H. Tetrahedron 1985, 41(18):3679-3682.
186. Desrut M., Kergomard A., Renard M.F., Veschambre H. Tetrahedron 1981, 37(22):3825-3829.
187. Hoegberg H., Hedenstroem E., Faegerhag J., Servi S. J. Org. Chem. 1992, 57(7):2052-2059.
188. Thanos I., Deffner A., Simon H. Biol. Chem. Hoppe-Seyler 1988, 369(1):451-460.
189. Fronza G., Fuganti C., Serra S. Eur. J. Org. Chem. 2009, 2009(35):6160-6171.
190. Gramatica P., Manitto P., Monti D., Speranza G. Tetrahedron 1988, 44(4):1299-1304.
191. Gil G., Ferre E., Barre M., Petit J. Tetrahedron Lett. 1988, 29(31):3797-3798.
192. Schwab J.M., Linn D.C.T. J. Am. Chem. Soc. 1985, 107(21):6046-6052.
193. Utaka M., Konishi S., Mizuoka A., et al. J. Org. Chem. 1989, 54(21):4989-4992.
194. Utaka M., Konishi S., Okubo T., Tsuboi S., Takeda A. Tetrahedron Lett. 1987, 28(13):1447-1450.
195. Kitazume T., Ishikawa N. Chemistry Lett. 1983, 12(2):237-238.
196. Ono N. The Nitro Group in Organic Synthesis 2001, Wiley-VCH, Weinheim.
197. Kawai Y., Inaba Y., Tokitoh N. Tetrahedron: Asymmetry 2001, 12(2):309-318.
198. Ohta H., Kobayashi N. J. Org. Chem. 1989, 54(8):1802-1804.
199. Takeshita M., Yoshida S., Kohno Y. Heterocycles 1994, 37(1):553-562.
200. Korbekandi H., Mather P., Gardiner J., Stephens G. Enzyme Microb. Technol. 2008, 42(4):308-314.
201. Mori A., Ishiyama I., Akita H., et al. Chem. Pharm. Bull. 1990, 38(12):3449-3451.
202. Bak R., McAnda A., Smallridge A., Trewhella M. Aust. J. Chem. 1996, 49(11):1257-1260.
203. Durchschein K., Ferreira-Da Silva B., Wallner S., et al. Green Chem. 2010, 12(4):616.
204. Ohta H., Ozaki K., Tsuchihashi G. Chem. Lett. 1987, 16(1):191-192.
205. Eich E. Solanaceae and Convolvulaceae: Secondary Metabolites Biosynthesis, Chemotaxonomy, Biological and Economic Significance: A Handbook 2008, Springer-Verlag, Berlin, pp 343-523.
206. Bhutani K., Thakur R. Phytochemistry 1991, 30(11):3599-3600.
207. Gramatica P., Manitto P., Monti D., Speranza G. Tetrahedron 1987, 43(19):2281-4486.
208. Gramatica P., Manitto P., Poli L. J. Org. Chem. 1985, 50(23):4625-4628.
209. Kupchan S.M., Eakin M.A., Thomas A.M. J. Med. Chem. 1971, 14(12):1147-1152.
210. Clark A., Hufford C. J. Chem. Soc. Perkin Trans. 1 1979, (12):3022-3028.
211. Gramatica P., Manitto P., Ranzi B., Delbianco A., Francavilla M. Experientia 1982, 38(7):775-776.
212. Grogan G., Holland H. J. Mol. Catal. B: Enzym. 2000, 9(1-3):1-32.
213. Noma Y., Nonomura S. Agric. Biol. Chem. Tokyo 1974, 38(4):741-744.
214. Noma Y., Nonomura S., Ueda H., Tatsumi C. Agric. Biol. Chem. Tokyo 1974, 38(4):735-740.
215. Hirata T., Izumi S., Shimoda K., Hayashi M. J. Chem. Soc. Chem. Commun. 1993, 18:1426-1427.
216. Fronza G., Fuganti C., Pinciroli M., Serra S. Tetrahedron: Asymmetry 2004, 15(19):3073-3077.
217. Nakao Y., Yada A., Ebata S., Hiyama T. J. Am. Chem. Soc. 2007, 129(9):2428-2429.
218. Lee D., Kim D., Yun J. Angew. Chem., Int. Ed. 2006, 45(17):2785-2787.
219. Smallridge A., Ten A., Trewhella M. Tetrahedron Lett. 1998, 39(28):5121-5124.
220. Barna T., Khan H., Bruce N., et al. J. Mol. Biol. 2001, 310(2):433-447.
221. Herl V., Fischer G., Boetsch R., Mueller-Uri F., Kreis W. Planta Med. 2006, 72(12):1163-1165.
222. Fauve A., Kergomard A. Tetrahedron 1981, 37(5):899-901.
223. Eyssen H.J., Parmentier G. Am. J. Clin. Nutr. 1974, 27(11):1329-1340.
224. Lefebvre G., Schneider F., Germain P., Gay R. Tetrahedron Lett. 1974, 15(2):127-128.
225. Miller T., Hessler E. Biochim. Biophys. Acta 1970, 202(2):354-360.
226. Lefebvre G., Germain P., Raval G., Gay R. Phytochemistry 1974, 13(10):2125-2133.
227. Boonstra B., Rathbone D., Bruce N. Biomol. Eng. 2001, 18(2):41-47.
228. Bruce N., Wilmot C., Jordan K., et al. Arch. Microbiol. 1990, 154(5):465-470.
229. Craig D., Moody P., Bruce N., Scrutton N. Biochemistry 1998, 37(20):7598-7607.
230. Hailes A., Bruce N. Appl. Environ. Microbiol. 1993, 59(7):2166-2170.
231. Clark W., Kassick A., Plotkin M., Eldridge A., Lantos I. Org. Lett. 1999, 1(11):1839-1842.
232. Leuenberger H.G.W., Boguth W., Barner R., Schmid M., Zell R. Helv. Chim. Acta 1979, 62(2):455-463.