Resolution of racemic 2-chlorophenyl glycine with immobilized penicillin G acylase

Tetrahedron Asymmetry

Volumn 19, Issue 20, 2008, Pages 2363-2366

  Fadnavis, Nitin W ^a   Vedamayee Devi, Avala ^a   Swarnalatha Jasti, Lakshmi ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROPHENYL GLYCINE; ACETIC ACID DERIVATIVE; ALPHA AMINO (2 CHLOROPHENYL)ACETIC ACID; GLYCINE DERIVATIVE; N PHENYLACETYL DERIVATIVE; PENICILLIN AMIDASE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; HYDROLYSIS; PRIORITY JOURNAL; RACEMIZATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 56949098025     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.10.015     Document Type: Article

References (33)

1. Badorc, A; Frehel, D. U.S. Patent 4,847,265, 1989.
2. Daniel, A.; Ferrand, C.; Maffrand, J. P. U.S. Patent 4,529, 596, 1985.
3. Bakonyi, M.; Csatari nee Nagy, M.; Molnar, L.; Gajary, A.; Alattyani, E. PCT Int. Appl. WO 1998/051689, 1998.
4. Bousquet, A.; Musolino, A. PCT Int. Appl. WO/1999/018110, 1999.
5. Bakonyi, M.; Csatari nee Nagy, M. Molnar nee Bako, E. Gajary, A.; Alattyani, E. US Patent 6,180,793, 2001.
6. Mukarram, M. S. J.; Merwade, Y. A.; Khan, R. A. U.S. Patent 7,291, 735 B2, 2007.
7. Castaldi, G.; Barreca, G.; Bologna, A. U.S. Patent 7,329,751 B2, 2008.
8. Wang P.-Y., Chen T.-L., and Tsai S.-W. Enzyme Microbiol. Technol. 39 (2006) 930-935
9. Uhm K.-N., Lee S.-J., Kim H.-K., Kang H.-Y., and Lee Y. J. Mol. Catal. B: Enzym. 45 (2007) 34-38
10. Tadashi E., Nobuyasu O., Sayaka I., and Takashi S. Org. Biomol. Chem. 5 (2007) 1175-1176
11. Lin, S. S.-S.; Chen, C.-C.; U.S. Patent 2004/0176637A1, 2004.
12. Reddy, B. S. PCT Int. Appl. WO 2006/003671 A1, 2006.
13. Katoh, O.; Uragaki, T.; Nakamura, T. PCT Int. Appl. WO 0187819, 2001.
14. Asano, Y. European Patent EP1770166, 2007.
15. The immobilized enzyme has an activity of 190 units/g wet at 37 °C. One unit is defined as one micromole of penicillin G hydrolyzed per minute.
16. Wegman M., Janssen M., van Rantwijk F., and Sheldon R. Adv. Synth. Catal. 343 (2001) 559-576
17. Arroyo M., de la Mata I., Acebal C., and Castilĺon M. Appl. Microbiol. Biotechnol. 60 (2003) 507-514
18. Chandel A.K., Venkateswar Rao L., Lakshmi Narasu M., and Singh O.V. Enzyme Microbiol. Technol. 42 (2008) 199-207
19. van Langen L.M., van Rantwijk F., Svedas V.K., and Sheldon R.A. Tetrahedron: Asymmetry 11 (2000) 1077-1083
20. Fuganti C., Grasselli P., Seneci P.F., Servi S., and Casati P. Tetrahedron Lett. 27 (1986) 2061-2062
21. Fadnavis N.W., Sharfuddin M., and Vadivel S.K. Tetrahedron: Asymmetry 10 (1999) 4495-4500
22. Fadnavis N.W., Radhika K.R., and Vedamayee Devi A. Tetrahedron: Asymmetry 17 (2006) 240-244
23. Cardillo G., Tolomelli A., and Tomasini C. J. Org. Chem. 61 (1996) 8651-8654
24. Fadnavis N.W., Sharfuddin M., Vadivel S.K., and Bhalerao U.T. J. Chem. Soc., Perkin Trans. 1 (1997) 3577-3578
25. Landis, B. H.; Ng, J. S.; Topgi, R.; Yonan, E. E.; Wang, P. T. U.S. Patent 6,214,609, 2001.
26. Bossi A., Cretich M., and Righetti P.G. Biotechnol. Bioeng. 60 (1998) 454-461
27. Calleri E., Massolini G., Loiodice F., Fracchiolla G., Temporini C., Félix G., Tortorella P., and Caccialanza G. J. Chromatogr., A 958 (2002) 131-140
28. Basso A., Braiuca P., De Martin L., Ebert C., Gardossi L., and Linda P. Tetrahedron: Asymmetry 11 (2000) 1789-1796
29. Kawasaki M., Nakamura K., and Kawabata S. J. Mol. Catal. B: Enzym. 6 (1999) 447-451
30. Wimmer Z., Skouridou V., Zarevúcka M., Šaman D., and Kolisis F.N. Tetrahedron: Asymmetry 15 (2004) 3911-3917
31. Sharma S.K., Husain M., Kumar R., Samuelson L.A., Kumar J., Watterson A.C., and Parmar V.S. Pure Appl. Chem. 7 (2005) 209-226
32. Grabley, S. U.S. Patent 4,638,086, 1987.
33. The reported specific rotation of +115.6 in Ref. 11 may be due to contamination with (+)-camphor sulfonic acid. We have consistently obtained the product with a specific rotation of +89, and chiral HPLC analysis indicated an enantiomeric purity of >99%.