7668
T. Purkarthofer et al. / Tetrahedron 61 (2005) 7661–7668
10. Brown, D.; Griffith, D.; Rider, M. E.; Smith, R. C. J. Chem.
Soc., Perkin Trans. 1 1986, 455–463.
analysis: CHIRALCEL OD-H, n-heptane/2-propanol 95:5,
0.5 mL/min, 10 8C; ret. times: 16.3, 21.8 min).
11. (a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.;
Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett.
1998, 39, 2941–2944. (b) Collot, V.; Bovy, P. R.; Rault, S.
Tetrahedron Lett. 2000, 41, 9053–9057. (c) Yu, S.; Saenz, J.;
Srirangam, J. K. J. Org. Chem. 2002, 67, 1699–1702.
Acknowledgements
The authors would like to thank Wolfgang Skranc and
Marcel Wubbolts for scientific discussions and Birgit
¨
12. Glieder, A.; Weis, R.; Skranc, W.; Pochlauer, P.; Dreveny, I.;
Majer, S.; Schwab, H.; Gruber, K. Angew. Chem. 2003, 115,
4963–4966. Angew. Chem., Int. Ed. 2003, 42, 4815–4818.
13. (a) Downie, I. M.; Earle, M. J.; Heaney, H.; Shuhaibar, K. F.
Tetrahedron 1993, 49, 4015–4034. (b) Kolb, V. M.; Stupar,
J. W.; Janota, T. E.; Duax, W. L. J. Org. Chem. 1989, 54,
¨
¨
Krenn, Wernfried Haas and Martin Trotzmuller for
experimental work. Financial support by DSM Fine
Chemicals Austria is gratefully acknowledged. Research
Centre Applied Biocatalysis is funded by TIG (Technologie
Impulse Gesellschaft m.b.H.), Vienna, the Province of
Styria and the City of Graz.
´
2341–2346. (c) Marko, I. E.; Giles, P. R.; Tsukazaki, M.;
´
Chelle-Regnaut, I.; Gautier, A.; Brown, S. M.; Urch, C. J.
J. Org. Chem. 1999, 64, 2433–2439.
14. (a) Lumme, P. O. Suomen kem. 1960, B33, 87–93. (b)
Fringuelli, F.; Marino, G.; Savelli, G. Tetrahedron 1969, 25,
5815–5818. (c) Butler, A. R. J. Chem. Soc. 1970, B, 867–870.
15. (a) Gruber, K. Proteins: Struct. Funct. Genet. 2001, 44, 26–31.
(b) Dreveny, I.; Kratky, C.; Gruber, K. Protein Sci. 2002, 11,
292–300.
References and notes
1. (a) Albers, H.; Hamann, K. Biochem. Z. 1934, 269, 14–25. (b)
Becker, W.; Benthin, U.; Eschenhof, E.; Pfeil, E. Biochem. Z.
1963, 337, 156–166. (c) Becker, W.; Freund, H.; Pfeil, E.
Angew. Chem., Int. Ed. Engl. 1965, 4, 1079. (d) Effenberger,
F.; Ziegler, T.; Foerster, S. Angew. Chem. 1987, 99, 491–492.
Angew. Chem., Int. Ed. Engl. 1987, 99, 458–460. (e) Brussee,
J.; Roos, E. C.; van der Gen, A. Tetrahedron Lett. 1988, 29,
4485–4488.
16. Cieplak, P.; Cornell, W. D.; Bayly, C. I.; Kollman, P. A.
J. Comput. Chem. 1995, 16, 1357–1377.
17. Wohlfahrt, G.; Witt, S.; Hendle, J.; Schomburg, D.; Kalisz,
H. M.; Hecht, H. J. Acta Crystallogr. Sect. D 1999, 55,
969–977.
18. Gruber, K.; Gugganig, M.; Wagner, U. G.; Kratky, C. Biol.
Chem. 1999, 380, 993–1000.
2. (a) Effenberger, F.; Eichhorn, J.; Roos, J. Tetrahedron:
Asymmetry 1995, 6, 271–282. (b) Johnson, D. V.; Felfer, U.;
Griengl, H. Tetrahedron 2000, 56, 781–790. (c) Johnson,
D. V.; Fischer, R.; Griengl, H. Tetrahedron 2000, 56,
9289–9295. (d) Bu¨hler, H.; Bayer, A.; Effenberger, F. Chem.
Eur. J. 2000, 6, 2564–2571.
19. Case, D. A.; Pearlman, D. A.; Caldwell, J. W.; Cheatham, T.
E., III; Ross, W. S.; Simmerling, C. L.; Darden, T. A.; Merz, K.
M.; Stanton, R. V.; Cheng, A. L.; Vincent, J. J.; Crowley, M.;
Ferguson, D. M.; Radmer, R. J.; Seibel, G. L.; Singh, U. C.;
Weiner, P. K.; Kollman, P.A. in AMBER 6.0; University of
California: San Francisco, CA, 1997.
3. (a) Fechter, M. H.; Griengl, H. Enzymatic Synthesis of
Cyanohydrins. In Enzyme Catalysis in Organic Synthesis;
Drauz, K., Waldmann, H., Eds.; Wiley-VCH: Weinheim,
2002; pp 974–989. (b) Gregory, R. J. H. Chem. Rev. 1999, 99,
3649–3682. (c) North, M. Tetrahedron: Asymmetry 2003, 14,
147–176.
20. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart,
W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19,
1639–1662.
21. Solis, F. J.; Wets, R. J. B. Math. Oper. Res. 1981, 6, 19–30.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven,
T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.;
Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.;
Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara,
M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.;
Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.;
Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.;
Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.;
Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala,
P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg,
J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain,
M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.;
Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.;
Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.;
Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.
L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.;
Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson,
B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. in
Gaussian 03, revision B.4, Gaussian, Inc., Pittsburgh, PA,
2003.
4. (a) Zandbergen, P.; van der Linden, J.; Brussee, J.; van der
Gen, A. Synth. Commun. 1991, 21, 1387–1391. (b) Schmidt,
´
M.; Herve, S.; Klempier, N.; Griengl, H. Tetrahedron 1996,
52, 7833–7840. (c) Effenberger, F.; Eichhorn, J. Tetrahedron:
Asymmetry 1997, 8, 469–476. (d) Griengl, H.; Klempier, N.;
¨
Pochlauer, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova,
A. A. Tetrahedron 1998, 54, 14477–14486.
5. Lin, G.; Han, S.; Li, Z. Tetrahedron 1999, 55, 3531–3540.
6. Chen, P.; Han, S.; Lin, G.; Huang, H.; Li, Z. Tetrahedron:
Asymmetry 2001, 12, 3273–3279.
7. (a) Gruber, K.; Gartler, G.; Krammer, B.; Schwab, H.; Kratky,
C. J. Biol. Chem. 2004, 279, 20501–20510. (b) Dreveny, I.;
Gruber, K.; Glieder, A.; Thompson, A.; Kratky, C. Structure
2001, 9, 803–815.
8. (a) Bray, B. L.; Muchowski, J. M. J. Org. Chem. 1988, 53,
6115–6118. (b) Bray, B. L.; Mathies, P. H.; Naef, R.; Solas,
D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. J. Org.
Chem. 1990, 55, 6317–6328.
9. Guida, W. C.; Mathre, D. J. J. Org. Chem. 1980, 45,
3172–3176.