Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of α- and β-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic β-Aminophosphonic Acids

Advanced Synthesis and Catalysis

Volumn 345, Issue 12, 2003, Pages 1287-1298

  Woschek, A ^a   Lindner, Wolfgang ^b   Hammerschmidt, F ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b Institute of Analytical Chemistry   (Austria)

Author keywords

Aminophosphonic acids; Enantioselectivity; Hydrolases; Hydroxyphosphonates; Kinetic resolution

Indexed keywords

ACETIC ACID DERIVATIVE; FUNGAL ENZYME; HYDROLASE; ISOPROTEIN; PHOSPHONIC ACID DERIVATIVE; PROTEINASE; SUBTILISIN; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CANDIDA CYLINDRACEA; CATALYSIS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 1642576230     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303135     Document Type: Article

References (50)

1. Part 10: F. Hammerschmidt, W. Lindner, F. Wuggenig, E. Zarbl, Tetrahedron: Asymmetry 2000, 11, 2955-2964.
2. U. T. Bornscheuer, R. J. Kazlauskas, Hydrolases in Organic Synthesis, Wiley-VCH, Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, 1999; K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis, Vols. I and II, VCH, Weinheim, New York, Basel, Cambridge, Tokyo, 1995; K. Faber, Biotransformations in Organic Chemistry, Springer Verlag, Berlin, Heidelberg, New York, London, Paris, Tokyo, Hong Kong, Barcelona, Budapest, 1992.
3. U. T. Bornscheuer, R. J. Kazlauskas, Hydrolases in Organic Synthesis, Wiley-VCH, Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, 1999; K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis, Vols. I and II, VCH, Weinheim, New York, Basel, Cambridge, Tokyo, 1995; K. Faber, Biotransformations in Organic Chemistry, Springer Verlag, Berlin, Heidelberg, New York, London, Paris, Tokyo, Hong Kong, Barcelona, Budapest, 1992.
4. U. T. Bornscheuer, R. J. Kazlauskas, Hydrolases in Organic Synthesis, Wiley-VCH, Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, 1999; K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis, Vols. I and II, VCH, Weinheim, New York, Basel, Cambridge, Tokyo, 1995; K. Faber, Biotransformations in Organic Chemistry, Springer Verlag, Berlin, Heidelberg, New York, London, Paris, Tokyo, Hong Kong, Barcelona, Budapest, 1992.
5. R. Zurawinski, K. Nakamura, J. Drabowicz, P. Kielbasinski, M. Mikołajczyk, Tetrahedron: Asymmetry 2001, 12, 3139-3145.
6. Y. Zhang, C. Yuan, Z. Li, Tetrahedron 2002, 58, 2973-2978.
7. a) M. Drescher, F. Hammerschmidt, H. Kählig, Synthesis 1995, 1267-1272;
8. b) G. Eidenhammer, F. Hammerschmidt, Synthesis 1996, 748-754.
9. K. Laumen, M. P. Schneider, J. Chem. Soc. Chem. Commun. 1988, 598-600.
10. F. Hammerschmidt, F. Wuggenig, Tetrahedron: Asymmetry 1999, 10, 1709-1721.
11. M. Kitamura, M. Tokunaga, and R. Noyori, J. Am. Chem. Soc. 1995, 117, 2931-2932.
12. I. Gautier, V. Ratovelomanana-Vidal, P. Savignac, J.-P. Genet, Tetrahedron Lett. 1996, 37, 7721-7724; G. Michaud, M. Bulliard, L. Ricard, J.-P. Genet, A. Marinetti, Chem. Eur. J. 2002, 8, 3327-3330.
13. I. Gautier, V. Ratovelomanana-Vidal, P. Savignac, J.-P. Genet, Tetrahedron Lett. 1996, 37, 7721-7724; G. Michaud, M. Bulliard, L. Ricard, J.-P. Genet, A. Marinetti, Chem. Eur. J. 2002, 8, 3327-3330.
14. C. Meier, W. H. G. Laux, J. W. Bats, Liebigs Ann. Chem. 1995, 1963-1979.
15. E. Zymanczczyk-Duda, B. Lejczak, P. Kafarski, Tetrahedron 1995, 51, 11809-11814.
16. C. Wawrzenczyk, J. Zon, E. Leja, Phosphorus, Sulfur, and Silicon 1992, 71, 179-184.
17. Z. Zhao, P. Liu, K. Murakami, T. Kuzuyama, H. Seto, H. Liu, Angew. Chem. 2002, 114, 4711-4714; Angew. Chem. Int. Ed. 2002, 41, 4529-4532.
18. Z. Zhao, P. Liu, K. Murakami, T. Kuzuyama, H. Seto, H. Liu, Angew. Chem. 2002, 114, 4711-4714; Angew. Chem. Int. Ed. 2002, 41, 4529-4532.
19. G. Guanti, M. T. Zannetti, L. Banfi, R. Riva, Adv. Synth. Catal. 2001, 343, 682-691.
20. J. F. Dellaria, Jr., R. G. Maki, Tetrahedron Lett. 1986, 27, 2337-2340; M. Ordonez, R. de la Cruz, M. Fernandez-Zertuche, M.-A. Munoz-Hernandez, Tetrahedron: Asymmetry 2002, 13, 559-562.
21. J. F. Dellaria, Jr., R. G. Maki, Tetrahedron Lett. 1986, 27, 2337-2340; M. Ordonez, R. de la Cruz, M. Fernandez-Zertuche, M.-A. Munoz-Hernandez, Tetrahedron: Asymmetry 2002, 13, 559-562.
22. T. Kamiya, K. Hemmi, H. Takeno, M. Hashimoto, Tetrahedron Lett. 1980, 21, 95-98.
23. T. Kuzuyama, T. Shimizu, S. Takahashi, H. Seto, Tetrahedron Lett. 1998, 39, 7913-7916.
24. K. Nakamura, T. Kimura, E. Takahashi, Phosphorus, Sulfur and Silicon 1999, 144-146, 613-616; K. Nakamura, S. Yamamura, Tetrahedron Lett. 1997, 38, 437-438.
25. K. Nakamura, T. Kimura, E. Takahashi, Phosphorus, Sulfur and Silicon 1999, 144-146, 613-616; K. Nakamura, S. Yamamura, Tetrahedron Lett. 1997, 38, 437-438.
26. a) W. S. Wadsworth, Jr., Org. React. 1977, 25, 73-253;
27. b) F. Mathey, P. Savignac, Tetrahedron 1978, 34, 649-654;
28. M. Baboulene, G. Sturtz, Phosphorus and Sulfur 1979, 7, 101-107;
29. D. G. Genov, J. C. Tebby, J. Org. Chem. 1996, 61, 2454-2459.
30. M. Drescher, Y.-F. Li, F. Hammerschmidt, Tetrahedron 1995, 51, 4933-4946.
31. F. Hammerschmidt, Monatshefte Chem. 1991, 122, 389-398.
32. D. Parker, Chem. Rev. 1991, 91, 1441-1457.
33. F. Hammerschmidt, Y. F. Li, Tetrahedron: Asymmetry 1994, 5, 10253-10264.
34. J. S. Kittredge, R. R. Hughes, Biochemistry 1964, 3, 991-996.
35. E. D. Korn, D. G. Dearborn, H. M. Fales, E. A. Sokoloski, J. Biol. Chem. 1973, 248, 2257-2259; F. Hammerschmidt, Liebigs Ann. Chem. 1988, 537-542.
36. E. D. Korn, D. G. Dearborn, H. M. Fales, E. A. Sokoloski, J. Biol. Chem. 1973, 248, 2257-2259; F. Hammerschmidt, Liebigs Ann. Chem. 1988, 537-542.
37. L. Widler, K. A. Jaeggi, M. Glatt, K. Müller, R. Bachmann, M. Bisping, A-R. Born, R. Cortesi, G. Guiglia, H. Jeker, R. Klein, U. Ramseier, J. Schmid, G. Schreiber, Y. Seltenmeyer, J. R. Green, J. Med. Chem. 2002, 45, 3721-3738.
38. R. E. Dolle, T. F. Herpin, Y. C. Shimshock, Tetrahedron Lett. 2001, 42, 1855-1858; D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett. 1990, 31, 5591-5594. D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, W. L. Rogers, S. A. Smith, J. M. DeForrest, R. S. Oehl, E. W. Petrillo, Jr., J. Med. Chem. 1995, 38, 4557-4569.
39. R. E. Dolle, T. F. Herpin, Y. C. Shimshock, Tetrahedron Lett. 2001, 42, 1855-1858; D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett. 1990, 31, 5591-5594. D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, W. L. Rogers, S. A. Smith, J. M. DeForrest, R. S. Oehl, E. W. Petrillo, Jr., J. Med. Chem. 1995, 38, 4557-4569.
40. R. E. Dolle, T. F. Herpin, Y. C. Shimshock, Tetrahedron Lett. 2001, 42, 1855-1858; D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett. 1990, 31, 5591-5594. D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, W. L. Rogers, S. A. Smith, J. M. DeForrest, R. S. Oehl, E. W. Petrillo, Jr., J. Med. Chem. 1995, 38, 4557-4569.
41. J. M. Varlet, N. Collignon, P. Savignac, Tetrahedron 1981, 37, 3713-3721.
42. M. E. Duggan, D. S. Karanewsky, Tetrahedron Lett. 1983, 24, 2935-2938.
43. M. Mikołajczyk, P. Lywa, J. Drabowicz, M. W. Wiecorek, J. Blaszczyk, J. Chem. Soc. Chem. Commun. 1996, 1503-1504.
44. F. Hammerschmidt, H. Völlenkle, Liebigs Ann. Chem. 1989, 577-583.
45. T. Gajda, M. Nowalinska, S. Zawadzki, A. Zwierzak, Phosphorus, Sulfur and Silicon, 1995, 105, 45-50.
46. E. Zarbl, M. Lämmerhofer, F. Hammerschmidt, F. Wuggenig, M. Hanbauer, N. M. Maier, L. Sajovic, W. Lindner, Anal Chim. Acta 2000, 404, 169-177.
47. W. Mikenda, Vibrational Spectroscopy 1992, 3, 327-330.
48. A: H. Ford-Moore, B. J. Perry, Organic Syntheses Coll. Vol. 4, 1963, 325-327.
49. Y.-F. Li, F. Hammerschmidt, Tetrahedron: Asymmetry 1993, 4, 109-120.
50. F. Hammerschmidt, Liebigs Ann. Chem. 1988, 531-535.