The quest for new mild and selective modifications of natural structures: Laccase-catalysed oxidation of ergot alkaloids leads to unexpected stereoselective C-4 hydroxylation

Chemistry - A European Journal

Volumn 18, Issue 33, 2012, Pages 10355-10361

  Chirivì, Cosimo ^a   Fontana, Gabriele ^b   Monti, Daniela ^a,c   Ottolina, Gianluca ^a,c   Riva, Sergio ^a,c   Danieli, Bruno ^d  

^a CNR   (Italy)

^b INDENA S P A   (Italy)

^c Centro Interuniversitario di Biotecnologie Proteiche   (Italy)

^d UNIVERSITY OF MILAN   (Italy)

Author keywords

alkaloids; biocatalysis; laccase; oxidation; stereoselectivity

Indexed keywords

ALKALOIDS; BENZYLIC; BIOCATALYSIS; ERGOT ALKALOIDS; FUNCTIONALISATION; HYDROXYDERIVATIVE; LACCASES; METHOXY; NATURAL STRUCTURES; NMR TECHNIQUES; SELECTIVE MODIFICATION; STEREO-SELECTIVE; STRUCTURE DETERMINATION;

CATALYSIS; HYDROXYLATION; METABOLITES; OXIDATION; STEREOSELECTIVITY;

NITROGEN COMPOUNDS;

ERGOT ALKALOID; LACCASE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

CATALYSIS; ERGOT ALKALOIDS; HYDROXYLATION; LACCASE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84864592277     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201076     Document Type: Article

References (41)

1. V. Kren, L. Cvak, Ergot -The Genus Claviceps, Medicinal and Aromatic Plants-Industrial Profiles, Harwood Academic Publishers, Amsterdam, London, 1999
2. B. Berde, H. O. Schild, Ergot and Related Compounds, Springer, Berlin, 1978.
3. G. Palmisano, G. Lesma, B. Danieli, G. Fiori, Synthesis 1987, 2, 137-139
4. B. Danieli, G. Fiori, G. Lesma, G. Palmisano, Tetrahedron Lett. 1983, 24, 819-820.
5. R. Gazak, V. Kren, P. Sedmera, D. Passarella, M. Novotna, B. Danieli, Tetrahedron 2007, 63, 10466-10478.
6. L. Quintanar, C. Stoj, A. B. Taylor, P. J. Hart, D. J. Kosman, E. I. Solomon, Acc. Chem. Res. 2007, 40, 445-452.
7. D. Monti, G. Ottolina, G. Carrea, S. Riva, Chem. Rev. 2011, 111, 4111-4140
8. N. Santhanam, J. M. Vivanco, S. R. Decker, K. F. Reardon, Trends Biotechnol. 2011, 29, 480-489
9. C. J. Rodgers, C. F. Blanford, S. R. Giggens, P. Skamnioti, F. A. Armstrong, S. J. Gurr, Trends Biotechnol. 2010, 28, 63-72
10. P. Giardina, V. Faraco, C. Pezzella, A. Piscitelli, S. Vanhulle, G. Sannia, Cell. Mol. Life Sci. 2010, 67, 369-385
11. S. Riva, Trends Biotechnol. 2006, 24, 219-226.
12. P. Gavezzotti, C. Navarra, S. Caufin, B. Danieli, P. Magrone, D. Monti, S. Riva, Adv. Synth. Catal. 2011, 353, 2421-2430
13. C. Navarra, C. Goodwin, S. Burton, B. Danieli, S. Riva, J. Mol. Catal. B 2010, 65, 52-57
14. R. Gažák, P. Sedmera, M. Marzorati, S. Riva, V. Křen, J. Mol. Catal. B 2008, 50, 87-92
15. C. Ponzoni, E. Beneventi, M. R. Cramarossa, S. Raimondi, G. Trevisi, U. M. Pagnoni, S. Riva, L. Forti, Adv. Synth. Catal. 2007, 349, 1497-1506
16. S. Ncanana, L. Baratto, L. Roncaglia, S. Riva, S. G. Burton, Adv. Synth. Catal. 2007, 349, 1507-1513
17. A. Intra, S. Nicotra, S. Riva, B. Danieli, Adv. Synth. Catal. 2005, 347, 973-977
18. S. Nicotra, M. R. Cramarossa, A. Mucci, U. M. Pagnoni, S. Riva, L. Forti, Tetrahedron 2004, 60, 595-600
19. S. Nicotra, A. Intra, G. Ottolina, S. Riva, B. Danieli, Tetrahedron: Asymmetry 2004, 15, 2927-2931.
20. F. Sagui, C. Chirivì, G. Fontana, S. Nicotra, D. Passarella, S. Riva, B. Danieli, Tetrahedron 2009, 65, 312-317.
21. F. Minisci, F. Recupero, A. Cecchetto, C. Gambarotti, C. Punta, R. Faletti, R. Paganelli, G. F. Peduli, Eur. J. Org. Chem. 2004, 1, 109-119
22. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071
23. S. A. Tromp, I. Matijosite, R. A. Sheldon, I. W. C. E. Arends, G. Mul, M. T. Kreutzer, J. A. Moulijn, S. de Vries, ChemCatChem 2010, 2, 827-833
24. I. W. C. E. Arends, Y. X. Li, R. Ausan, R. A. Sheldon, Tetrahedron 2006, 62, 6659-6665
25. C. Galli, P. Gentili, J. Phys. Org. Chem. 2004, 17, 973-977
26. M. Fabbrini, C. Galli, P. Gentili, J. Mol. Catal. B 2002, 18, 169-171
27. P. Baiocco, A. M. Barreca, M. Fabbrini, C. Galli, P. Gentili, Org. Biomol. Chem. 2003, 1, 191-197.
28. M. Fabbrini, C. Galli, P. Gentili, D. Macchitella, Tetrahedron Lett. 2001, 42, 7551-7553
29. A. Potthast, T. Rosenau, C. L. Chen, J. S. Gratzl, J. Mol. Catal. A 1996, 108, 5-9
30. F. d'Acunzo, P. Baiocco, M. Fabbrini, C. Galli, P. Gentili, Eur. J. Org. Chem. 2002, 24, 4195-4201.
31. C. Chirivì, F. Sagui, S. Riva, in Practical methods for biocatalysis and biotransformations (Eds:, J. Whittall, P. W. Sutton,), Wiley, Chichester, 2010, pp. 240-244
32. L. Baratto, A. Candido, M. Marzorati, F. Sagui, S. Riva, B. Danieli, J. Mol. Catal. B 2006, 39, 3-8
33. M. Marzorati, B. Danieli, D. Haltrich, S. Riva, Green Chem. 2005, 7, 310-315.
34. K. Schnatbaum, H. J. Schafer, Synthesis 1999, 5, 864-872.
35. C. S. Gomez-Bujedo, E. Fleury, M. R. Mignon, Macromolecules 2004, 37, 565-571
36. C. Fraschini, M. R. Vignon, Carbohydr. Res. 2000, 328, 585-589.
37. A. Potthast, T. Rosenau, C. L. Chen, J. S. Gratzl, J. Org. Chem. 1995, 60, 4320-4321
38. E. Fritz-Langhals, B. Kunath, Tetrahedron Lett. 1998, 39, 5955-5956
39. A. Coniglio, C. Galli, P. Gentili, R. Vadalà, J. Mol. Catal. B 2008, 50, 40-49
40. X. Hu, P. Wang, H. Hwang, Bioresour. Technol. 2009, 100, 4963-4968
41. T. Orbegozo, I. Lavandera, W. M. F. Fabian, B. Mautner, J. G. de Vries, W. Kroutil, Tetrahedron 2009, 65, 6805-6809.