Resolution of anti-3-oxotricyclo[2.2.1.0]heptane-7-carboxylic acid by Candidia antartica lipase A

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 3975-3976

  Kingery Wood, Jill ^a   Johnson, Jeffrey S ^a  

^a BAYER CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 OXOTRICYCLO[2.2.1.0]HEPTANE 7 CARBOXYLIC ACID; POLYCYCLIC HYDROCARBON; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; DRUG PURIFICATION; ENANTIOMER; ENZYME ACTIVITY;

CANDIDA; CANDIDIA;

EID: 0030015127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00759-9     Document Type: Article

References (15)

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2. b) Stanek, J; Ledvinova, M.; Vesely, I.; Vladimir, V.; Karel, J.; Mostecky, J; Palecek, J.; Kubelka, V. Czech. CS 240 862, 1985; Chem. Abstr. 110:231177.
3. b) Stanek, J; Ledvinova, M.; Vesely, I.; Vladimir, V.; Karel, J.; Mostecky, J; Palecek, J.; Kubelka, V. Czech. CS 240 862, 1985; Chem. Abstr. 110:231177.
4. c) Beeley, N. R. A.; Peel, R.; Sutherland, J. K.; Holohan, J. J.; Mallion, K. B.; Sependa, G. J. Tetrahedron, Suppl. No. 1, 1981, 37, 411-20.
5. d) Greico, P. A.; Owens, W.; Wang, C.-L. J.; Williams, E.; Schillinger, W. J. J. Med. Chem. 1980, 23, 1072-1077.
6. e) Greico, P. A.; Ohfune, Y.; Yokoyama, Y.; Owens, W. J. Am. Chem. Soc. 1979, 101, 4749-4752.
7. f) Bindra, J. S; Grodski, A.; Schaaf, T. K.; Corey, E. J. J. Am. Chem. Soc. 1973, 95, 7522-7523.
8. Enzymes were purchased from the following sources: Sigma: Candidia cylindracea (L-1754); porcine pancreatic lipase (L-3126); Pseudomonas fluorescens (P-6380); PLE (E-3128); SC (P-5380); cholesterol esterase (C-3766); Acetyl cholinesterase (C-2629); Amano: PS30 Lipase; Altus Biologics, Inc: CA-A lipase and ChiroCLEC-CR.
9. No difference in selectivity between the two esters was seen, only the methyl ester was pursued.
10. A ChiroScreen-EH kit from Altus Biologics Inc., 40 Allston Street, Cambridge, MA, 02139-4211. All of the enzymes in the kit are available individually from Altus Biologics Inc.
11. 3) δ 1.49 (t, J = 5.2 Hz, 1 H), 1.86 (d, J = 11.4 Hz, 1 H); 1.98 (d, J = 11.0 Hz, 1 H); 2.25 (m, 2 H), 2.41 (t, J = 5.2 Hz, 1 H); 3.02 (s, 1 H); 3.71 (s, 3 H).
12. R for (-)-3, 13.1 min, (+)-3, 15.0 min, (-)-1, 20.5 min, (+)-1, 25.6 min.
13. CLEC = Cross-Linked Enzyme Crystals: a) Lalonde, J. J.; Govardhan, C.; Khalaf, N.; Martinez, A. G.; Visuri, K.; Margolin, A. L. J. Am. Chem. Soc. 1995, 117, 6845-6852.
14. b) St. Clair, N. L.; Navia, M. A. J. Am. Chem. Soc. 1992, 114, 7314-7316.
15. 4 then filtered and concentrated in vacuo to give 2.82 g (34%) of the desired (-)-1.