Regioselective enzymatic acylation as a tool for producing solution- phase combinatorial libraries

Tetrahedron

Volumn 54, Issue 16, 1998, Pages 3971-3982

  Mozhaev, Vadim V ^c   Budde, Cheryl L ^a   Rich, Joseph O ^a   Usyatinsky, Alexander Ya ^a   Michels, Peter C ^a   Khmelnitsky, Yuri L ^a   Clark, Douglas S ^b   Dordick, Jonathan S ^c  

^a EnzyMed Inc   (United States)

^b University of California   (United States)

^c UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BERGENIN; FLAVONOID;

BIOSYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CONFERENCE PAPER; DRUG SYNTHESIS; ENZYME ACTIVITY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0032537029     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00129-X     Document Type: Conference Paper

References (28)

1. 1. Keinan, E.; Sinha, S. C.; Sinha-Bagch, A. J. Chem. Soc. Perkins Trans. 1 1991, 3333-3339.
2. 2. Patel, R. N.; Robison, R. S.; Szarka, L. J.; Kloss, J.; Thottathil, J.K.; Mueller, R.H. Enzyme Microb. Technol 1991, 13, 906-912.
3. 3. Kieslich, K. Steroid Conversions. In Economic Microbiology 5: Microbial Enzymes and Bioconversions; Rose A. H., Ed.; Academic Press: London, 1980; pp. 369-465.
4. 4. Kiener, A. US Patent 5, 104, 798, 1992.
5. 5. Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093-3096.
6. 6. Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Amer. Chem. Soc. 1990, 112, 2849-2854.
7. 7. Saksena, A. K.; Girijavallabhan, V. M.; Wang, H.; Liu, Y. T.; Pike, R. E.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 5657-5660.
8. 8. Drauz, K.; Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook; VCH: Weinheim, 1995.
9. 1H-and C-NMR and mass spectrometry (see Experimental section).
10. 10. Verdine, G. L. Nature, 1996, 384, 11-13.
11. 11. Michels, P. C.; Khmelnitsky, Yu. L.; Dordick, J. S.; Clark, D. S. Trends Biotech. 1997, in press.
12. 12. Khmelnitsky, Yu. L.; Michels, P. C.; Dordick, J. S.; Clark, D. S. Generation of Solution-Phase Libraries of Organic Molecules by Combinatorial Biocatalysis. In Molecular Diversity and Combinatorial Chemistry; Chaiken, I. M.; Janda, K. D., Eds.; American Chemical Society: Washington, D. C., 1996; pp. 144-157.
13. 13. Alting-Mees, M. A.; Sorge, J. A.; Short, J. M. pBluescriptII: Multifunctional Cloning and Mapping Vectors. In Recombinant DNA Methodology II; Wu, R., Ed.; Academic Press: San Diego, 1995; pp. 171-183.
14. 14. Macferrin, K. D.; Chen, L.;Terranova,M. P.; Schreiber, S. L.; Verdine, G. L. Meth. Enzymol. 1993, 217, 79-102.
15. 15. Roessner, C. A.; Spencer, J. B.; Ozaki, S.; Min, C.; Atshaves, B. P.; Nayar, P.; Anousis, N.; Stolowich, N. J.; Holderman, M. T.; Scott, A. I. Protein Expr. Purif. 1995, 6, 155-163.
16. 16. Fisher, C. W., Manjunath, S. S.; Estabrook, R. W. Meth. Enzymol. 1996, 272, 15-24.
17. 17. Smith, M. C.; Furman, T. C.; Ignolia, T. D.; Pidgeon, C. J. Biol Chem. 1988, 263, 7211-7215.
18. 18. Stemmer, W. P. C. Nature 1994, 370, 389-391.
19. 19. Kast, P.; Hilvert, D. Pure Appl. Chem., 1996, 68, 2017-2024.
20. 20. Moore, J. C.; Arnold, F. H. Nature Biotechnol. 1996,14, 458-467.
21. 21. Arnold, F. H. Chem. Eng. Sci. 1996, 51, 5091-5102.
22. 22. Zhang, J. H.; Dawes, G.; Stemmer, W. P. C. Proc. Nat. Acad. Sci. USA 1997, 94, 4504-4509.
23. 23. Jacobsen, J. R.; Hutchinson, C. R.; Cane, D. E.; Kholsa, C. Science 1997, 277, 367-369.
24. 24. Svensson, I; Wehtje, E.; Adlercreutz, P.; Mattiasson, B. Biotechnol. Bioeng. 1994, 44, 549-556.
25. 25. Khmelnitsky, Yu. L.; Welch, S. H.; Clark, D. S.; Dordick, J. S. J. Amer. Chem. Soc. 1994, 116, 2647-2648.
26. 26. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6477-6484.
27. 27. Jahodar, L.; Kolb, I.; Lyska, A. Fitoterapia 1992, 63, 260-261.
28. 28. Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem.Soc. Perkins Trans. 1, 1979, 2313-2316.