Synthesis, test and application of chirale fluorescence substrates to evaluate enzymatic processes in different reaction media

Enzyme and Microbial Technology

Volumn 37, Issue 7, 2005, Pages 673-686

  Knüttel, Torsten ^a,b   Meyer, Hartmut ^a   Scheper, Thomas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b Amersham Health   (Norway)

Author keywords

Chymotrypsin; 2D fluorescence spectroscopy; Coumarines; Enantioselective hydrolysis; Esterase; On line monitoring

Indexed keywords

BIOLOGICAL ORGANS; ENZYMES; ESTERS; HYDROLYSIS; OPTIMIZATION; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

2D-FLUORESCENCE SPECTROSCOPY; COUMARINES; ENANTIOSELECTIC HYDROLYSIS; ESTERASE; ON-LINE MONITORING;

FLUORESCENCE;

CHYMOTRYPSIN A; COUMARIN DERIVATIVE; DEXTRO PHENYLALANINE 7 AMIDO 4 METHYLCOUMARIN; DEXTRO PHENYLALANINE 7 AMIDO 4 TRIFLUOROMETHYLCOUMARIN; ESTERASE; ORGANIC SOLVENT; PROTEINASE; TOLUENE; UNCLASSIFIED DRUG;

ANALYTICAL PARAMETERS; AQUEOUS SOLUTION; ARTICLE; BIOCATALYST; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME SUBSTRATE; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; HYDROLYSIS; LIVER; ONLINE MONITORING; REACTION ANALYSIS; SWINE; SYNTHESIS;

SUIDAE; TRIFLUORO;

EID: 25444528238     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2004.04.026     Document Type: Article

References (25)

1. A. Liese, K. Seelbach, and C. Wandrey Industrial biotransformations 2000 Wiley-VCH Weinheim
2. H.E. Schoemaker, D. Mink, and M.G. Wubbolts Dispelling the myths - biocatalysis in industrial synthesis Science 299 2003 1694 1697
3. U. Bornscheuer, A. Capewell, V. Webdel, and T. Scheper On-line determination of the conversion in a lipase-catalyzed kinetic resolution in supercritical carbon dioxide J Biotechnol 46 1996 139 143
4. M. Konarzycka-Bessler, and U. Bornscheuer A high-throughput-screening method for determining the synthetic activity of hydrolases Angew Chem Int Ed 42 12 2003 1418 1420
5. F. Moris-Varas, A. Shah, J. Aikens, N.P. Nadkarni, J.D. Rozzel, and D.C. Demirjian Visualization of enzyme-catalyzed reactions using pH indicators: rapid screening of hydrolase libraries and estimation of the enantioselectivity Bioorg Med Chem 7 1999 2183 2188
6. T. Knüttel, T. Hartmann, H. Meyer, and T. Scheper On-line monitoring of a quasi-enantiomeric reaction with two coumarine substrates via 2D-fluorescence spectroscopy Enzyme Microb Technol 29 2001 150 159
7. S. Ueji, K. Watanabe, T. Koshiba, M. Nakamura, K. Oh-ishi, and Y. Yasufuku Lipase-catalyzed esterification of 2-(4-substituted phenoxy)propionic acids in organic solvents: substituent effect controlling enantioselectivity toward racemic acids Biotechnol Lett 21 1999 865 868
8. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih Quantitative analyses of biochemical kinetic resolutions of enantiomers J Am Chem Soc 104 1982 7294 7299
9. T. Scheper, K. Schügerl, and M. Weiss To new fluorogenic substrates fort he detection of penicillin-G-acylase activity Anal Chim Acta 182 1986 203 206
10. R. O'Kennedy, and R.D. Thornes Coumarines: biology; application and mode of action 1997 John Wiley & Sons Ltd.
11. Scheper T, Schügerl K, Weiss M. Patent PS 3614647 (1988).
12. K. Kuromizu, Y. Shimokawa, O. Abe, and N. Izumiya New fluorogenic substrate for esterase activity of α-chymotrypsin and related enzymes Anal Biochem 151 1985 534 539
13. K. Watanabe, T. Koshiba, Y. Yasufuku, T. Miyazawa, and S. Ueji Effects of substituents and temperature on enantioselectivity for lipase-catalyzed esterification of 2-(4-substituted phenoxy) propionic acids in organic solvents Bioorg Chem 29 2 2001 65 76
14. H. Kise, and T. Nagashima Enantiospecificity of chymotrypsin at S′1 site for peptide synthesis in aqueous-organic media Bull Chem Soc Jpn 66 1993 3693 3698
15. T. Nagashima, A. Watanabe, and H. Kise Peptide synthesis by proteases in organic solvents: medium effect on substrate specificity Enzyme Microb Technol 14 1992 1118 1123
16. C. Laane Medium-engineering for bioorganic synthesis Biocatalysis 1 1987 17 22
17. K. Laszlo, and L.M. Simon Chymotrypsin-catalyzed synthesis of N-acetyl-l-tyrosine esters in organic media Stabil Stabilization Biocatalysts 1998 713 718
18. M.O. Mansson, M. Stahl, and K. Mosbach Induced stereo and substrate selectivity of bio-imprinted chymotrypsin in anhydrous organic media Biocatal Non-conventional media 1992 321 327
19. V.V. Mozhaev Engineering stability of enzymes in systems with organic solvents Stabil Stabilisation Biocatalysts 1998 355 363
20. G.R. Castro Enzymatic activities of proteases dissolved in organic solvents Enzyme Microb Technol 25 1999 689 694
21. J. Partridge, B.D. Moore, and P.J. Halling α-Chymotrypsin stability in aqueous-acetonitrile mixtures: is the native enzyme thermodynamically or kinetically stable under low water conditions? J Mol Catal B: Enzym 6 1999 11 20
22. V. Laroute, and R.M. Willemot Effect of organic solvents on stability of two glycosidases and gluco-amylase catalysed oligosaccharides synthesis Enzyme Microb Technol 14 1992 528 534
23. M.V. Filho, T. Stillger, M. Müller, A. Liese, and C. Wandrey Is log P a convenient criterion to guide the choice of solvents for biphasic enzymatic reactions? Angew Chem Int Ed 42 2003 2993 2996
24. S. Ruppert, and H.J. Gais Activity enhancement of pig liver esterase in organic solvents by colyophilization with methoxypolyethylene glycol: kinetic resolution of alcohols Tetrahedron: Asymm 8 21 1997 3657 3664
25. K. Buchholz, and V. Kasche Biokatalysatoren und enzymtechnologie 1997 Wiley-VCH Weinheim