Enzymatic kinetic resolution of pantolactone: Relevance to chiral auxiliary chemistry

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1697-1701

  Haughton, Louise ^a   Williams, Jonathan M J ^a   Zimmermann, Jochen A ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; FUNGAL ENZYME; PANTOLACTONE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ENZYME KINETICS; ENZYME MECHANISM; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0034608115     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00130-0     Document Type: Article

References (15)

1. Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 1-21.
2. Whitesell, J. K.; Lawrence, R. M. Chimia 1986, 9, 318-321.
3. Schwartz, A.; Madan, P.; Whitesell, J. K.; Lawrence, R. M. Org. Synth. 1990, 69, 1-9.
4. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095-3098.
5. Gamalevich, G. D.; Serebryakov, E. P. Russian Chemical Bulletin 1997, 46, 171-183.
6. Shimizu, S.; Kataoka, M. Ann. NY Acad. Sci. 1996, 799, 650-658.
7. Bevinakatti, H. S.; Banerji, A. A.; Newadkar, R. V. J. Org. Chem. 1989, 54, 2453-2455.
8. Vilenchik, L. Z.; Griffith, J. P.; St. Clair, N. L.; Navia, M. A.; Margolin, A. L. J. Am. Chem. Soc. 1998, 120, 4290-4294.
9. St. Clair, N. L.; Navia, M. A. J. Am. Chem. Soc. 1992, 114, 7314-7316.
10. Altus 20 from Altus Biologics Inc., 40 Allston Street, Cambridge, MA 02139-4211, USA.
11. Using a gammadex column from Supelco, the pantolactone acetate enantiomers were separated at 110°C with retention times of 16.48 min (R) and 17.57 min (S). Other enzymes examined for the conversion of pantolactone into pantolactone acrylate include Altus 17 (CRL), lipases from Candida antarctica, Pseudomonas cepecia, and Pseudomonas fluorescens, and hog liver esterase and α-chymotrypsin, but none of these afforded any significant conversion.
12. Margolin, A. L.; Fitzpatrick, P. A.; Dubin, P. L.; Klibanov, A. M. J. Am. Chem. Soc. 1991, 113, 4693-4694. Acrylate esters of oximes have been used in enzyme-catalysed acylation reactions: Athawale, V.; Manjrekar, N. Synlett 2000, 225-226.
13. Margolin, A. L.; Fitzpatrick, P. A.; Dubin, P. L.; Klibanov, A. M. J. Am. Chem. Soc. 1991, 113, 4693-4694. Acrylate esters of oximes have been used in enzyme-catalysed acylation reactions: Athawale, V.; Manjrekar, N. Synlett 2000, 225-226.
14. 3)
15. Candida antarctica lipase (500kU, Chirazyme L-2 c.-f. C2, lyo) from Boehringer Mannheim.