Synthesis of Unsaturated C8-C9 Sugars by Enzymatic Chain Elongation

Synlett

Volumn 1996, Issue 2, 1996, Pages 138-140

  Kim, Mahn Joo ^a   Lim, In Taek ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011200842     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5357     Document Type: Article

References (28)

1. Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
2. Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
3. Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
4. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Holt, K. E.; Leeper, ; Handa, S.; J. Chem. Soc., Perkin Trans. 1 1994, 231. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585. Eyrisch, O.; Fessner, W.-D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1639 and references therein.
5. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Holt, K. E.; Leeper, ; Handa, S.; J. Chem. Soc., Perkin Trans. 1 1994, 231. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585. Eyrisch, O.; Fessner, W.-D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1639 and references therein.
6. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Holt, K. E.; Leeper, ; Handa, S.; J. Chem. Soc., Perkin Trans. 1 1994, 231. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585. Eyrisch, O.; Fessner, W.-D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1639 and references therein.
7. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Holt, K. E.; Leeper, ; Handa, S.; J. Chem. Soc., Perkin Trans. 1 1994, 231. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585. Eyrisch, O.; Fessner, W.-D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1639 and references therein.
8. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Holt, K. E.; Leeper, ; Handa, S.; J. Chem. Soc., Perkin Trans. 1 1994, 231. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585. Eyrisch, O.; Fessner, W.-D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1639 and references therein.
9. 3, ppm) 134.6, 117.3.102.1, 67.7,62.1, 61.4, 41.8, 39.8, 15.2, 15.1.
10. Jung, S. H.; Jeong, J. H.; Miller, P.; Wong, C. H. J. Org. Chem. 1994, 59, 7182.
11. From Sigma (RAMA, product number A 7145; Pase, product number P 1146).
12. +) 227.0895, found 227.0901.
13. Durrwachter, J. R.; Wong, C.-H. J. Org. Chem. 1988, 53, 4175. Bednarski, M. D.; Simon, E. S.; Bischofberger, N.; Fessner, W.-D.; Kim, M.-J.; Lees, W.; Saito, T.; Waldmann, H.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 627. Liu, K. K.-C.; Pederson, R. L.; Wong, C. H. J. Chem. Soc. Perkin Trans. 1 1991, 2669.
14. Durrwachter, J. R.; Wong, C.-H. J. Org. Chem. 1988, 53, 4175. Bednarski, M. D.; Simon, E. S.; Bischofberger, N.; Fessner, W.-D.; Kim, M.-J.; Lees, W.; Saito, T.; Waldmann, H.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 627. Liu, K. K.-C.; Pederson, R. L.; Wong, C. H. J. Chem. Soc. Perkin Trans. 1 1991, 2669.
15. Durrwachter, J. R.; Wong, C.-H. J. Org. Chem. 1988, 53, 4175. Bednarski, M. D.; Simon, E. S.; Bischofberger, N.; Fessner, W.-D.; Kim, M.-J.; Lees, W.; Saito, T.; Waldmann, H.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 627. Liu, K. K.-C.; Pederson, R. L.; Wong, C. H. J. Chem. Soc. Perkin Trans. 1 1991, 2669.
16. 3). The absolute configuration was assigned based on the sterochemical preference of lipase AK established previously. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
17. +) 227.0895, found 227.0919
18. Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahderon Lett. 1991, 32, 4775.
19. 3, ppm) 117.3, 101.7, 64.6, 63.0, 62.2, 39.2, 25.8, 15.2, 15.1.
20. +) 226.0691, found 226.0706.
21. 3). The absolute configuration was assigned as described in ref. 8.
22. +) 226.0691, found 226.0710.
23. w = 0.046, GOF = 0.41. Data for X-ray crystallographic analysis were measured on a Enraf-Nonius CAD4 diffractometer using Mo Kα radiation at room temperature. The structures were solved by a direct method (SHELX86) and refined anisotropically by full-matrix least-square methods.
24. Very recently, it was observed that some RAMA-catalyzed reactions took place with incomplete 3S, 4R stereoselectivity to give the major product of 35,4R configuration and the minor product of 3S,4S configuration. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947.
25. Unnatural stereoselectivities have also been reported for other aldolases. Fessner, W.-D.; Sinerius, G.; Schneider, A.; Dreyer, M.; Schulz, G. E.; Badia, J.; Aguilar, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 555. Gautheron-Le Narvor, C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113. Fessner, W.-D.; Eyrisch, O. Angew. Chem. Int. Ed. Engl. 1992, 31, 56. Lin, C.-H.; Sugai, R. L.; Halcomb, Y.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138.
26. Unnatural stereoselectivities have also been reported for other aldolases. Fessner, W.-D.; Sinerius, G.; Schneider, A.; Dreyer, M.; Schulz, G. E.; Badia, J.; Aguilar, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 555. Gautheron-Le Narvor, C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113. Fessner, W.-D.; Eyrisch, O. Angew. Chem. Int. Ed. Engl. 1992, 31, 56. Lin, C.-H.; Sugai, R. L.; Halcomb, Y.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138.
27. Unnatural stereoselectivities have also been reported for other aldolases. Fessner, W.-D.; Sinerius, G.; Schneider, A.; Dreyer, M.; Schulz, G. E.; Badia, J.; Aguilar, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 555. Gautheron-Le Narvor, C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113. Fessner, W.-D.; Eyrisch, O. Angew. Chem. Int. Ed. Engl. 1992, 31, 56. Lin, C.-H.; Sugai, R. L.; Halcomb, Y.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138.
28. Unnatural stereoselectivities have also been reported for other aldolases. Fessner, W.-D.; Sinerius, G.; Schneider, A.; Dreyer, M.; Schulz, G. E.; Badia, J.; Aguilar, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 555. Gautheron-Le Narvor, C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113. Fessner, W.-D.; Eyrisch, O. Angew. Chem. Int. Ed. Engl. 1992, 31, 56. Lin, C.-H.; Sugai, R. L.; Halcomb, Y.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138.