Application of polymer-supported enzymes and reagents in the synthesis of γ-aminobutyric acid (GABA) analogues

Synlett

Volumn , Issue 10, 2002, Pages 1641-1644

  Baxendale, Ian R ^a   Ernst, Martin ^a   Krahnert, Wolf Rüdiger ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Desymmetrisation; GABA analogues; Pig liver esterase; Polymer supported enzymes; Polymer supported reagents

Indexed keywords

4 AMINOBUTYRIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ELASTASE; LIVER ENZYME; POLYMER; REAGENT; SCAVENGER;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; FILTRATION; REACTION ANALYSIS; SWINE;

EID: 0036400032     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34249     Document Type: Article

References (40)

1. (a) Mohr, P.; Waespe-Sarcevic, N.; Tamm, C.; Gawronska, K.; Gawronski, J. K. Helv. Chim. Acta 1983, 66, 2501.
2. (b) Walser, P.; Renold, P.; N'Goka, V.; Hosseinzadeh, F.; Tamm, C. Helv. Chim. Acta 1991, 74, 1941.
3. (c) Schneider, M.; Engel, N.; Hönicke, P.; Heinemann, G.; Görisch, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 67.
4. (a) Mosbach, K. FEBS Lett. 1976, 62, E80.
5. (b) Worsfold, P. Pure Appl. Chem. 1995, 67, 597.
6. (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815.
7. (b) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650.
8. (c) Guino, M.; Brule, E.; De Miguel, Y. R. Chimica Oggi-Chem. Today 2002, 20, 23.
9. (d) Ley, S. V.; Baxendale, I. R.; Brusotti, G.; Caldarelli, M.; Massi, A.; Nesi, M. Farmaco 2002, 57, 321.
10. (a) Allan, R. D.; Curtis, D. R.; Headley, P. M.; Johnston, G. A. R.; Lodge, D.; Twitchin, B. J. J. Neurochem. 1980, 34, 652.
11. (b) Kusama, T.; Spivak, C. E.; Whiting, P.; Dawson, V. L.; Schaeffer, J. C.; Uhl, G. R. Br. J. Pharmacol. 1993, 109, 200.
12. (c) Kusama, T.; Wang, T.-L.; Guggino, W. B.; Cutting, G. R.; Uhl, G. R. Eur. J. Pharmacol. 1993, 245, 83.
13. Allan, R. D.; Johnston, G. A. R. Med. Res. Rev. 1983, 3, 91.
14. (a) Kennewell, P. D.; Matharu, S. S.; Tazlor, J. B.; Westwood, R.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1982, 2563.
15. (b) Paulini, K.; Reissig, H.-U. Liebigs Ann. Chem. 1991, 455.
16. (c) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97.
17. (d) Galeazzi, R.; Mobili, G.; Orena, M. Tetrahedron: Asymmetry 1997, 8, 133.
18. (e) Duke, R. K.; Allan, R. D.; Chebib, M.; Greenwood, J. R.; Johnston, G. A. R. Tetrahedron: Asymmetry 1998, 9, 2533.
19. (f) Forti, L.; Ghelfi, F.; Levizzani, S.; Pagnoni, U. M. Tetrahedron Lett. 1999, 40, 3233.
20. (g) Bonnaud, B.; Cousse, H.; Mouzin, G.; Briley, M.; Stenger, A.; Fauran, F.; Couzinier, J.-P. J. Med. Chem. 1987, 30, 318.
21. (h) Galeazzi, R.; Mobili, G.; Orena, M. Tetrahedron 1999, 8, 261.
22. Purchased from Fluka Cat. No. 46064; solid support: methacrylamide/allyl glycidylether/methylene-bisacrylamide; loading: ∼500 U/g.
23. 1a
24. Born, M.; Tamm, C. Synthesis 1991, 435.
25. Purchased from Aldrich Cat. No. 21,644-5.
26. Purchased from Fluka Cat. No. 81393; solid support: poly(4-vinylpyridine)/25% DVB.
27. Purchased from Aldrich Cat. No. 36,834-2; solid support: styrene/DVB; loading: 3.8 mmol/g.
28. Purchased from Fluka Cat. No. 57895; solid support: styrene/>20% DVB; loading: 2.9 mmol/g.
29. Purchased from Fluka Cat. No. 93093; solid support: styrene/2% DVB; loading: 3 mmol/g.
30. Purchased from Novabiochem Cat. No. 01-64-0178; solid support: styrene/1% DVB; loading 2.0-3.5 mmol/g.
31. 6d
32. 1a
33. 25 = -17.4 (c 0.8, CHCl3). Crystallographic data of the amide formed from 12a and (+)-α-methylbenzylamine have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-189257. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(1223)336033; deposit@ccdc.cam.ac.uk).
34. 3), which is the opposite of the rotations published in references 1a,c.
35. 13C NMR spectrum the ratio of the diastereomers is 1:1.7.
36. Purchased from Novabiochem Cat. No. 01-64-0177; solid support: styrene/2% DVB; loading: 2.0-3.0 mmol/g.
37. 25 = 3.3 (C 1.1, MeOH).
38. Purchased from Novabiochem Cat. No. 01-64-0170; solid support: styrene/1% DVB; loading: 2.2 mmol/g.
39. 6h
40. Soai, K.; Yokoyama, S.; Mochida, K. Synthesis 1987, 647.