Chiral heteroatom-containing compounds

Future Directions in Biocatalysis

Volumn , Issue , 2007, Pages 159-203

  Kiełbasiński, Piotr ^a   Mikołajczyk, Marian ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882917363     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-044453059-2/50009-1     Document Type: Chapter

References (143)

1. Mikołajczyk M, Drabowicz J, Kiełbasiński P. Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis 1997, CRC Press, Boca Raton.
2. Pietrusiewicz K.M., Zabłocka M Chem. Rev. 1994, 94:1375-1411.
3. Kafarski P, Lejczak B. Phosphorus Sulfur Silicon 1991, 63:193-215.
4. Palacios F, Alonso C, de los Santos J.M. Chem. Rev. 2005, 105:899-931.
5. Kiełbasiński P, Mikołajczyk M. Hydrolytic Enzymes in the Synthesis of Non-racemic Heteroorganic Compounds with a Stereogenic Centre on the Heteroatom. Enzymes in Action: Green Solutions for Chemical Problems 2000, 161-191. Kluwer, Dordrecht. B. Zwanenburg, M. Mikołajczyk, P. Kiełbasiński (Eds.).
6. Holland H. Chem. Rev. 1988, 88:473-485.
7. Colonna S, Gaggero N, Richelmi C, Pasta P. Enantioselective Oxidations Catalyzed by Peroxidases and Monooxygenases. Enzymes in Action: Green Solutions for Chemical Problems 2000, 133-160. Kluwer, Dordrecht. B. Zwanenburg, M. Mikołajczyk, P. Kiełbasiński (Eds.).
8. Holland H.L., Brown F.M., Lozada D, Mayne B, Szerminski W.R,, van Vliet, A Can. J. Chem. 2002, 80:633-639.
9. Bakker M, van Rantwijk F, Sheldon R.A. Can. J. Chem. 2002, 80:622-625.
10. Hodgson D, Buist P.H. Tetrahedron Asymm. 2003, 14:641-644.
11. Milton J, Brand S, Jones M.F., Rayner C.M. Tetrahedron Asymm. 1995, 6:1903-1906.
12. Milton J, Brand S, Jones M.F., Rayner C.M. Tetrahedron Lett. 1995, 36:6961-6964.
13. Brand S, Jones M.F., Rayner C.M. Tetrahedron Lett. 1995, 36:8493-8496.
14. Brand S, Jones M.F., Rayner C.M. Tetrahedron Lett. 1997, 38:3595-3598.
15. Csuk R, Glanzer B.I. Chem. Rev. 1991, 91:49-97.
16. Servi S. Synthesis 1990, 1-25.
17. Crumbie R.L., Deol B.S., Nemorin J.E., Ridley D.D. Aust. J. Chem. 1978, 31. 1965.
18. Iriuchijima S,, Kojima N. Agric. Biol. Chem. 1978, 42:451.
19. Yamazaki T, Asai M, Ohnogi T, Lin J.T,, Kitazume T J. Fluorine Chem. 1987, 35:537.
20. Itoh T,, Nakai M,, Sato T. Tetrahedron Lett. 1985, 26:771-774.
21. Fujisawa T,, Kojima E,, Itoh T,, Sato T. Chem. Lett. 1985, 1751-1754.
22. Han C.Q., Di Tullio D, Wang Y.F,, Sih C J. J. Org. Chem. 1986, 51:1253-1258.
23. Takaishi Y, Yang Y.L,, Di Tullio D,, Sih C J. Tetrahedron Lett. 1982, 23:5489-5492.
24. Guanti G, Banfi L, Guaragna A, Narisano E. J. Chem. Soc., Chem. Commun. 1986, 138-139.
25. Guanti G,, Banfi L,, Narisano E. Tetrahedron Lett. 1986, 27:3547-3550.
26. Ghiringhelli D. Tetrahedron Lett. 1983, 24:287-290.
27. Urban F.J., Breitenbach R, Vincent L.A. J. Org. Chem. 1990, 55:3670-3672.
28. Lemaire M,, Bolte J. Tetrahedron Asymm. 1999, 10:4755-4762.
29. Robin S,, Huet F,, Fauve A,, Veschambre H. Tetrahedron Asymm. 1993, 4:239-243.
30. Kozikowski A.P., Mugrage B.B., Li C.S,, Felder L Tetrahedron Lett. 1986, 27:4817-4820.
31. Ohta H, Kato Y, Tsuchihashi G.I. J. Org. Chem. 1987, 52:2735-2739.
32. Tanikaga R, Hosoya K, Kaji A. J. Chem. Soc. Perkin Trans. I 1987, 1799-1803.
33. Nakamura K, Ushio K, Oka S, Ohno A, Yasui S. Tetrahedron Lett. 1984, 25:3979-3982.
34. Chinchilla R,, Najera C,, Pardo J,, Yus M. Tetrahedron Asymm. 1990, 1:575-578.
35. Kiełbasiński P, Rachwalski M, Mikołajczyk M, Moelands M.A.H., Zwanenburg B, Rutjes F.P.J.T. Tetrahedron Asymm. 2005, 16:2157-2160.
36. Menasche N, Shvo Y. Organometallics 1991, 10:3885-3891.
37. Huerta F.F., Minidis A.B.E., Backvall J.-E Chem. Soc. Rev. 2001, 30:321-331.
38. Kiełbasiński P, Rachwalski M, Mikołajczyk, M. Unpublished results.
39. von Meyer E. J. Prakt. Chem. 1901, 63:167.
40. Field L, Settlage P.H. J. Am. Chem. Soc. 1951, 73:5870-5872.
41. Bredereck H,, Bader E. Chem. Ber. 1954, 87:129.
42. Faber K,, Kroutil W. Curr. Opin. Chem. Biol. 2005, 9:181-187.
43. Boltes I, Czapińska H, Kahnert A, von Bulow R, Dierks T, Schmidt B, von Figura K, Kertesz M.A., Uson I Structure 2001, 9:483-491.
44. Faber K, Glueck S.M., Nestl B.M, Larisseger-Schnell B, Wallner S.R., Kroutil W. BIOTRANS 2005, (July 3-8):1. 2005, Delft, NL, Abstract book.
45. Pogorevc M, Kroutil W, Wallner S.R,, Faber K Angew. Chem. Int. Ed. Engl. 2002, 41:4052-4054.
46. Pogorevc M,, Faber K. Tetrahedron Asymm. 2002, 13:1435-1441.
47. Pogorevc M, Strauss U.T,, Riemeier T,, Faber K Tetrahedron Asymm. 2002, 13:1443-1447.
48. Wallner S.R., Nestl B.M., Faber K Org. Lett. 2004, 6:5009-5010.
49. Wallner S.R., Nestl B.M,, Faber K Tetrahedron 2005, 61:1517-1521.
50. Kiełbasiński P, Albrycht M, Mikołajczyk M, Wieczorek M.W., Majzner W.R,, Filipczak A,, Ciołkiewicz P Heteroatom Chem. 2005, 16:93-103.
51. Ohta H,, Tsuchihashi G. Chem. Lett. 1986, 217-218.
52. Burgess K,, Henderson I. Tetrahedron Lett. 1989, 30:3633-3636.
53. Burgess, K Henderson I, Ho K.-K J. Org. Chem. 1992, 57:1290-1295.
54. Kiełbasiński P. Tetrahedron Asymm. 2000, 11:911-915.
55. Cardellicchio C,, Naso F,, Scilimati A. Tetrahedron Lett. 1994, 35:4635-4638.
56. Allenmark S.G., Andersson A.C. Tetrahedron Asymm. 1993, 4:2371-2376.
57. Kiełbasiński P, Mikołajczyk M, Zwanenburg B, de Laet R.C. Phosphorus Sulfur Silicon 1994, 95-96:495-496.
58. Kiełbasiński P, Zwanenburg B, Damen T.J.G., Wieczorek M.W., Majzner W.R., Bujacz G Eur. J. Org. Chem. 1999, 2573-2578.
59. Mikołajczyk M, Kiełbasiński P, Zurawiński R, Wieczorek M.W., Błaszczyk J. Synlett 1994, 127-129.
60. Wieczorek M.W., Błaszczyk J, Mikołajczyk M, Kiełbasiński P, Zurawiński R Heteroatom Chem. 1994, 5:167-173.
61. Tamai S, Miyauchi S, Morizane C, Miyagi K, Shimizu H, Kume M, Sano S, Shiro M, Nagao Y. Chem. Lett. 1994, 2381-2384.
62. Serreqi A.N,, Kazlauskas R J. Can. J. Chem. 1995, 73:1357-1367.
63. Morita S, Matsubara J, Otsubo K, Kitano K, Ohtani T, Kawano Y, Uchida M. Tetrahedron Asymm. 1997, 8:3707-3710.
64. Kitano K, Matsubara J, Ohtani T, Otsubo K, Kawano Y, Morita S, Uchida M. Tetrahedron Lett. 1999, 40:5235-5238.
65. 44. Kiełbasiński, P; Albrycht M, Mikołajczyk, M. Unpublished results.
66. Medio-Simon M, Gil J, Alemon P, Varea T, Asensio G. Tetrahedron Asymm. 1999, 10:561-566.
67. Holland H.L,, Ihasz N,, Lounsbery B J. Can. J. Chem. 2002, 80:640-642.
68. Saville C.K., Magloire V.P., Kazlauskas R J. J. Am. Chem. Soc. 2005, 127:2104-2113.
69. Mugford P.F., Magloire V.P,, Kazlauskas R J. J. Am. Chem. Soc. 2005, 127:6536-6537.
70. Our parallel experiments, in which subtilisin Carlsberg was used to promote hydrolysis of N-acetyl-N-benzyl arenesulfinamides, led to exclusive S-N bond breaking. However, the recovered substrates were racemic. Moreover, blank experiments showed that a spontaneous chemical hydrolysis contributed to the process to a much higher degree than that in the cases shown in Ref. 47. Hence, a conclusion was drawn that in our case the hydrolysis proceeded without involvement of the subtilisin active site: Kiełbasiński P, Albrycht M, Mikołajczyk, M. Unpublished results.
71. Mugford P.F., Kazlauskas R.J. BIOTRANS 2005, 243. July 3-8, 2005, Delft, NL, Abstract book.
72. Kiełbasiński P. Pol. J. Chem. 1999, 73:735-738.
73. Toone E.J., Werth M.J., Jones J.B. J. Am. Chem. Soc. 1990, 112:4946-4952.
74. Zymańczyk-Duda E, Lejczak B, Kafarski P, Grimaud J, Fischer P. Tetrahedron 1995, 51:11809-11814.
75. Zymańczyk-Duda E, Kafarski P, Lejczak B. Enzym. Microbiol. Technol. 2000, 26:265-270.
76. Kafarski P,, Lejczak B. J. Mol. Catal. B Enzym. 2004, 29:99-104.
77. Brzezińska-Rodak M, Zymańczyk-Duda E, Kafarski P, Lejczak B. Biotechnol. Prog. 2002, 18:1287-1291.
78. Yuan C,, Wang K,, Li Z. Heteroatom Chem. 2001, 12:551-556.
79. Mikołajczyk M, Łuczak J, Kiełbasiński P. J. Org. Chem. 2002, 67:7872-7875.
80. Zurawiński R, Nakamura K, Drabowicz J, Kiełbasiński P, Mikołajczyk M. Tetrahedron Asymm. 2001, 12:3139-3145.
81. Ramos Tombo G.M,, Bellus D Angew. Chem. Int. Ed. Engl. 1991, 30:1193-1215.
82. Kagan H.B., Tahar M, Fiaud J.-C Tetrahedron Lett. 1991, 32:5959-5962.
83. Khushi T, O'Toole K.J., Sime J.T. Tetrahedron Lett. 1993, 34:2375-2378.
84. Li Y.-F,, Hammerschmidt F Tetrahedron Asymm. 1993, 4:109-120.
85. Drescher M,, Hammerschmidt F,, Kahlig H. Synthesis 1995, 1267-1272.
86. Eidenhammer G,, Hammerschmidt F. Synthesis 1996, 748-754.
87. Hammerschmidt F,, Wuggenig F. Tetrahedron Asymm. 1999, 10:1709-1721.
88. Skwarczyński M,, Lejczak B,, Kafarski P. Chirality 1999, 11:109-114.
89. Zhang Y, Yuan C, Li Z. Tetrahedron 2002, 58:2973-2978.
90. Pamies O, Backvall J.-E J. Org. Chem. 2003, 68:4815-4818.
91. Patel R.N,, Banerjee A,, Szarka L J. Tetrahedron Asymm. 1997, 8:1055-1059.
92. Kitamura M, Tokunaga M, Noyori R. J. Am. Chem. Soc. 1995, 117:2931-2932.
93. Aboujaoude E.E., Collignon N, Savignac P, Teulade M.P. Phosphorus, Sulfur, Silicon 1985, 25:57-61.
94. Zhang Y,, Li Z,, Yuan C. Tetrahedron Lett. 2002, 43:3247-3249.
95. Yokomatsu T, Nakabayashi N, Matsumoto K, Shibuya S. Tetrahedron Asymm. 1995, 6:3055-3062.
96. Yokomatsu T, Sato M, Shibuya S. Tetrahedron Asymm. 1996, 7:2743-2754.
97. Attolini M, Iacazio G, Peiffer G, Charmasson Y, Maffei M. Tetrahedron Asymm. 2004, 15:827-830.
98. Zhang Y,, Xu C,, Li J,, Yuan C. Tetrahedron Asymm. 2003, 14:63-70.
99. Solodenko V.A., Kasheva T.N., Kukhar V.P., Kozlova E.V., Mironenko D.A., Svedas V.S. Tetrahedron 1991, 47:3989-3998.
100. Yuan C, Xu C, Zhang Y. Tetrahedron 2003, 59:6095-6112.
101. Heisler A, Rabiller C, Douillard R, Goalou N, Hagele G, Levayer F. Tetrahedron Asymm. 1993, 4:959-960.
102. Heisler A, Rabiller C, Hagele G. Phosphorus, Sulfur, Silicon 1995, 101:273-280.
103. Hammerschmidt F, Lindner W, Wuggenig F, Zarbl E. Tetrahedron Asymm. 2000, 11:2955-2964.
104. Fang J.-M, Lin C.-H, Bradshaw C.W., Wong C.-H J. Chem. Soc. Perkin Trans. I 1995, 967-978.
105. Natchev I. J. Chem. Soc. Perkin Trans. I 1989, 125-131.
106. Willms L, Fulling G, Keller, R. EP 0382113, 1990.
107. Willms L, Bartsch, K. EP 0690133, 1996.
108. Kiełbasiński P, Zurawiński R, Pietrusiewicz K.M,, Zabłocka M,, Mikołajczyk M Tetrahedron Lett. 1994, 35:7081-7084.
109. Kiełbasiński P, Zurawiński R, Pietrusiewicz K.M,, Zabłocka M,, Mikołajczyk M Pol. J. Chem. 1998, 72:564-572.
110. Kiełbasiński P, Góralczyk P, Mikołajczyk M, Wieczorek M.W., Majzner W.R. Tetrahedron Asymm. 1998, 9:2641-2650.
111. Sano S,, Kujime E,, Takemoto Y,, Shiro M,, Nagao Y. Chem. Pharm. Bull. 2005, 53:131-134.
112. Kiełbasiński P,, Zurawiński R,, Albrycht M,, Mikołajczyk M. Tetrahedron Asymm. 2003, 14:3379-3384.
113. Serreqi A.N,, Kazlauskas R J. J. Org. Chem. 1994, 59:7609-7615.
114. Spangler L.A., Mikołajczyk M, Burdge E.L., Kiełbasiński P, Smith H.C, Łyz wa P., Fisher J.D., Omelańczuk J. J. Agric. Food Chem. 1999, 47:318-321.
115. Kiełbasiński P,, Omelańczuk J,, Mikołajczyk M. Tetrahedron Asymm. 1998, 9:3283-3287.
116. Kiełbasiński P,, Albrycht M,, Łuczak J,, Mikołajczyk M. Tetrahedron Asymm. 2002, 13:735-738.
117. Albrycht M,, Kiełbasiński P,, Drabowicz J,, Mikołajczyk M,, Matsuda T,, Harada T,, Nakamura K. Tetrahedron Asymm. 2005, 16:2015-2018.
118. Shioji K,, Ueno Y,, Kurauchi Y,, Okuma K. Tetrahedron Lett. 2001, 42:6569-6571.
119. Shioji K,, Tashiro A,, Shibata S,, Okuma K. Tetrahedron Lett. 2003, 44:1103-1105.
120. Yamagishi T,, Miyamae T,, Yokomatsu T,, Shibuya S. Tetrahedron Lett. 2004, 45:6713-6716.
121. Kiełbasiński P, Zurawiński R, Bałczewski P, Mikołajczyk M. Alkylphosphorus Compounds. Comprehensive Organic Functional Group Transformations 2005, Vol. 2:383-461. Elsevier, Amsterdam. A.R. Katritzky, R.J.K. Taylor (Eds.).
122. Imamoto T. Pure Appl. Chem. 2001, 73:373.
123. Shioji K,, Kurauchi Y,, Okuma K. Bull. Chem. Soc. Jpn 2003, 76:833-834.
124. Kiełbasiński P,, Albrycht M,, Zurawiński R,, Mikołajczyk M. J. Mol. Catal. B Enzym. 2006, 39:45-49.
125. Wiktelius D, Johansson M.J,, Luthmann K,, Kann N Org. Lett. 2005, 7:4991-4994.
126. Dudman N,, Zerner B. J. Am. Chem. Soc. 1973, 95:3019-3021.
127. Munnecke D.M. Appl. Environ. Microbiol. 1976, 32:7-13.
128. Lewis V.E., Donarski W.J., Wild J.R., Raushel F.M. Biochemistry 1988, 27:1591-1597.
129. Wu F, Li W.S., Chen-Goodspeed M, Sogorb M.A., Raushel F.M. J. Am. Chem. Soc. 2000, 122:10206-10207.
130. Li Y, Aubert S.D., Raushel F.M. J. Am. Chem. Soc. 2003, 125:7526-7527.
131. Li Y, Aubert S.D., Maes E.G., Raushel F.M. J. Am. Chem. Soc. 2004, 126:8888-8889.
132. Li W.-S., Li Y., Hill C.M., Lum K.T., Raushel F.M. J. Am. Chem. Soc. 2002, 124:3498-3499.
133. Hill C.M., Wu F, Cheng T.-C, DeFrank J.J., Raushel F.M. Bioorg. Med. Chem. Lett. 2000, 10:1285-1288.
134. Hill C.M., Li W.-S, Cheng T.-C, DeFrank J.J., Raushel F.M. Bioorg. Chem. 2001, 29:27-35.
135. Jao, S.-C Huang, L.-F Tao, Y.-S Li W.-S J. Mol. Catal. B Enzym. 2004, 27:7-12.
136. Huang L.-F, Su B, Jao S.C., Liu K.-T, Li W.-S ChemBioChem 2006, 7:506-514.
137. Vanhooke J.L., Benning M.M., Raushel F.M., Holden H.M. Biochemistry 1996, 35:6020-6025.
138. Millard C.B., Lockridge O, Broomfield C.A. Biochemistry 1995, 34:15925-15933.
139. Lockridge O, Blong R.M., Masson P, Froment M.-T, Millard C.B., Broomfield C.A. Biochemistry 1997, 36:786-795.
140. Fukui T,, Kawamoto T,, Tanaka A. Tetrahedron Asymm. 1994, 5:73-82.
141. Djerourou A.H,, Blanco L Tetrahedron Lett. 1991, 32:6325-6326.
142. Tacke R,, Wagner S.A,, Sperlich J. Chem. Ber. 1994, 127:639-642.
143. Tacke R, Kosub U, Wagner S.A,, Bertermann R,, Schwarz S,, Merget S,, Gunther K Organometallics 1998, 17:1687-1699.