Lipase-catalyzed regioselective one-step synthesis of penta- O-acetyl-3-hydroxylactal

European Journal of Organic Chemistry

Volumn , Issue 20, 2009, Pages 3327-3329

  Filice, Marco ^a   Vanna, Renzo ^b   Terreni, Marco ^b   Guisan, Jose M ^a   Palomo, Jose M ^a  

^a CSIC   (Spain)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

Carbohydrates ; Enzyme catalysis; Hydrolysis ; Regioselectivity ; Supported catalysts

Indexed keywords

EID: 67650504067     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900357     Document Type: Article

References (25)

1. a) A. C. Weymouth-Wilson, Nat. Prod. Rep. 1997, 14, 99-110;
2. b) V. Kren, T. Rezanka, FEMS Microbiol. Rev. 2008, 32,858-889.
3. a) K. C. Nicolaou, S. Y. Cho, R. Hughes, N. Winssinger, C. Smethurst, H. Labischinski, R. Endermann, Chem. Eur. J. 2001, 7, 3798-3823;
4. b) C. E. Melancon III, W.-L. Yu, H.-w. Liu, J. Am, Chem, Soc. 2005, 127, 12240-12241.
5. G. J. Williams, R. W. Gantt, J. S. Thorson, Curr. Opin. Chem. Biol. 2008, 12, 556-564.
6. A. S. Rowan, C. J Hamilton, Nat. Prod. Rep. 2006, 23, 412443.
7. a) A. Ghanem, H. Y. Aboul-Enein, Chirality 2005, 17, 44-50;
8. b) C.-H. Wong, G. M. Whitesides, Enzymes in synthetic organic chemistry, Pergamon Press, Oxford, 1994.
9. a) U. T. Bornscheuer, Curr. Opin. Biotechnol. 2002, 13, 543547;
10. b) N. J. Turner, Curr. Opin, Biotechnol. 2003, 14, 401-406;
11. c) F.-W. Lou, B. K. Liu, Q. Wu, d.-S. Lv, X.-F. Lin, Adv. Synth. Catal. 2008, 350, 1959-1962.
12. a) M. Gamba, A. A. M. Lapis, J. Dupont, Adv. Synth. Catal. 2008, 350, 160-164;
13. b) S. Akai, K. Tanimoto, Y. Kanao, M. Egi, T. Yamamoto, Y. Kita, Angew. Chem. Int. Ed. 2006, 45, 2592-2595.
14. J. M. Palomo, Curr. Org. Synth. 2009, 6, 1-14.
15. U. Derewenda, A. M. Brzozowski, D. M. Lawson, Z. S. Derewenda, Biochemistry 1992, 31, 1532-1541.
16. a) C. Gervaise, R. Daniellou, C. Nugier-Chauvin, V. Ferneres, Tetrahedron Lett. 2009, 50, 2083-2085;
17. b) J. M. Palomo, M. Filice, R. Fernandez-Lafuente, M. Terreni, J. M. Guisan, Adv. Synth. Catal. 2007, 349,1969-1976;
18. c) A. A. Mendes, D. S. Rodrigues, M. Filice, R. Fernandez-Lafuente, J. M. Guisan, J. M. Palomo, Tetrahedron 2008, 64, 10721-10727;
19. d) M. Filice, T. Bavaro, R. Fernandez-Lafuente, M. Pregnolato, J. M. Guisan, J. M. Palomo, M. Terreni, Catal. Today 2009, 140, 11-18.
20. A. Bastida, P. Sabuquillo, P. Armisen, R. Fernandez-Lafuente, J. Huguet, J. M. Guisán, Biotechnol. Bioeng. 1998, 58, 486-493.
21. All the lipase-immobilized preparations were containing 4 mg of pure lipase per gram, of solid. For more details, see Supporting Information.
22. 3) ppm. 2D-COSY was used to assign the signals.
23. For the scale-up of the reaction to 8 g/L, 0.71 mmol of 1 was hydrolyzed in 50 mL of a solution of 50 mM sodium acetate (80%) and acetonitrile (20%) at pH 5 by using 5 g of octylRML preparation.
24. 14 (51.8.16): caled. C 50.96, H 5.83, O 43.20; found C 49.55, H 5.72, O 42.80.
25. H. M. Kim, I. J. Kim, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 35-48.