Selectivity paradigm in lipase reactions: Correlating actual and observed regioselectivity in hydrolysis of unsymmetrical diacetates

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8105-8107

  Desai, Shrivallabh B ^a   Argade, Narshinha P ^a   Ganesh, Krishna N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENZYME ACTIVITY; ENZYME SPECIFICITY; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033615629     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990598x     Document Type: Article

References (35)

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7. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
8. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
9. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
10. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
11. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
12. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
13. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
14. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
15. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
16. (a) Sugihara, J. M. Adv. Carbohydr. Chem. I 1953, 8, 1. (b) Angyal, S. J.; Melrose, G. J. H. J. Chem. Soc. 1965, 6494 and 6501. (c) Welsh, L. H. J. Org. Chem, 1967, 32, 119. Albert, R.; Dax, K.; Stuetz, A. E.; Weidman, H. J. Carbohydr. Chem. 1983, 2, 289. (e) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (f) Belluci, G.; Bianchini, R.; Vechiani, S. J. Org. Chem. 1987, 52, 3355. (g) Liu, K. K. C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1980, 3, 169. (h) Heisler, A.; Rabiller, C.; Hublin, L. Biotechnol. Lett. 1991, 13, 327. Millqvist-Fureby, A.; Virto, C.; Adlercreutz, P.; Mattiason, B. Biocatal. Biotransform. 1996, 14, 89. (j) D'Arrigo, P.; Servi, S. Trends Biotechnol. 1997, 15, 90. (k) Horrobin, T. H.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. 1 1998, 1069.
17. For a recent example on intermolecular acyl migration in the solid state see: Praveen, T.; Samanta, U.; Das, T.; Shashidhar, M. S.; Chakrabarti, P. J. Am. Chem. Soc. 1998, 120, 3842.
18. (a) Mattaon, F. H.; Beck, L. W. J. Biol. Chem. 1955, 214, 115. (b) Mattson, F. H.; Beck, L. W. J. Biol. Chem. 1956, 219, 735.
19. (a) Mattaon, F. H.; Beck, L. W. J. Biol. Chem. 1955, 214, 115. (b) Mattson, F. H.; Beck, L. W. J. Biol. Chem. 1956, 219, 735.
20. hd that sn-2 regioselectivity stems from acyl migration and an actual sn-2-specific lipase may not exist. Briand, D.; Duberucq, E.; Galzy, P. Eur. J. Biochem. 1995, 228, 169.
21. hd that sn-2 regioselectivity stems from acyl migration and an actual sn-2-specific lipase may not exist. Briand, D.; Duberucq, E.; Galzy, P. Eur. J. Biochem. 1995, 228, 169.
22. hd that sn-2 regioselectivity stems from acyl migration and an actual sn-2-specific lipase may not exist. Briand, D.; Duberucq, E.; Galzy, P. Eur. J. Biochem. 1995, 228, 169.
23. hd that sn-2 regioselectivity stems from acyl migration and an actual sn-2-specific lipase may not exist. Briand, D.; Duberucq, E.; Galzy, P. Eur. J. Biochem. 1995, 228, 169.
24. Brockerhoff, H. Biochim. Biophys. Acta 1968, 159, 296.
25. 1H NMR data reported by the authors for the p-nitro derivative of 8 fit in well with the alternate structure, i.e., thep-nitro derivative of 9, and our method will be directly useful to confirm actual and observed selectivities in this example.
26. Desai, S. B.; Argade, N. P.; Ganesh, K. N. J. Org. Chem. 1996, 61, 6730.
27. 1H NMR data (relative integrations of methyl group from -OAc).
28. The rate of enzymatic hydrolysis for (2S,3R)-4 was relatively faster (24 h) than for (±)-1 (156-180 h).
29. Menger, F. M.; Chen, X. Y.; Brocchini, S.; Hopkins, H. P.; Hamilton, D. J. Am. Chem. Soc. 1993, 115, 6600.
30. (a) Herradon, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron Assym. 1993, 4, 845. (b) Argazzoni, F.; Maconi, E.; Potenza, D.; Scolastico, C. Synthesis 1989, 225.
31. (a) Herradon, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron Assym. 1993, 4, 845. (b) Argazzoni, F.; Maconi, E.; Potenza, D.; Scolastico, C. Synthesis 1989, 225.
32. 1H NMR spectral data of the crude reaction products and column-purified products revealed that in both examples there was no intramolecular acyl migration during silica gel column chromatography.
33. The AmanoPS-and PLAP-catalyzed hydrolysis of (±)-7 was nonstereoselective; see: Taterie, N. H.; Bailey, R. A.; Kates, M. Arch. Biochem. Biophys. 1966, 78, 319.
34. PLAP-catalyzed hydrolysis of (±)-7 was arrested when the corresponding diol formation was detected upon TLC (∼25% conversion, 2 h).
35. Dupus, C.; Corre, C.; Boyaval, P. Appl. Environ. Microbiol. 1993, 59, 4004.