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1 Biocatalytic xidation of Alcohols FH Biotech Conference Leiden sabel Arends June 21, Biocatalysis Vermelding onderdeel and rganic organisatie Chemistry
2 Catalytic xidations Using 2, H 2 2 (acl) Peroxidases and oxidases Hybrid enzymes and biomimetic cats anocatalysts Directed Evolution of Enzymes Hydratases itrilases Biocatalysis and rganic Chemistry Prof. sabel Arends Dr. Fred van Rantwijk, Dr. Ulf Hanefeld Dr. Linda tten Chirotechnology Lipases and esterases Amidases itrilases June 21, xynitrilases n-situ racemisation Cascade reactions Catalysis in ovel Media Enzymes in onic Renewable Raw Materials liquids Carbohydrates ScC2 ionic Lipids liquids Terpenes
3 Aldehydes and ketones in the F&F and Pharmaceuticals ndustry H cumaldehyde Me H anisaldehyde nandrolon citral/citronellal hyacinth/rose smell (in tea, coffee, tobacco) June 21,
4 xidations (Dark Ages) 2 Cr H 2 S 4 - Cr 2 (S 4 ) 3-6 H H 2 3 Atom Utilisation = 44% vs. 87% ther favoured reagents: Dess-Martin Swern Ac Ac Ac Cl H 3 C S CH 3 June 21, R.A. Sheldon, J. Chem. Tech. Biotechnol. 68 (1997) 381
5 June 21, ALCLS ALDEHYDES H + ACTVE XYGE x CH 3 CH 3 PS n-situ generation of ()-polymer
6 Biocatalytic oxidation of alcohols Laccase: used in combination with mediators Alcohol oxidases galactose oxidase (Cu-based, slow) Alcohol oxidases (Flavin-cofactor) Alcohol dehydrogenases ADH cofactor June 21, Sheldon, Arends, Hanefeld, Green Chemistry and Catalysis (2007) Wiley.
7 Galactose xidase H H CH 2 H CH Galactose xidase H H 2 2 Proc atl Acad Sci USA. 2001, 98 (23), June 21,
8 Reactivity of substrates with Galactose xidase H galactose oxidase 100 aliphatic alcohols α,β-unsaturated alcohols aromatic alcohols H 75 H 3 C 32 Limited applicability Still rather slow H 3 C 4.8 H 3 C 3.4 b Cl 0.06 Ph b Cl F 2 H Cl H H Cl Cl Br 17 b b 3.2 Reviews: Arends, Gamez, Sheldon, Adv. in norg. Chem. Vol 58. (2006) Acad.press. pp. 235 Siebum, van Wijk, Schoevaart, Kieboom, J.Mol.Catal.B 41 (2006) 141. June 21, H 3.4 a 14
9 Mechanism Alcohol Dehydrogenases June 21,
10 Preparative alcohol oxidation by an ADH from R. ruber up to 1.8 mol L -1 R' + R' ADH R. ruber DSM AD + R' + R' 3.4 mol L -1 = 20 vol% W. Kroutil, H. Mang, K. Edegger, K. Faber, Adv. Synth. Catal. 346 (2004) 125. June 21,
11 June 21,
12 Laccase: an oxidase enzyme laccase 2 Substrate-H Substrate (ox) + 2 H 2 Glycosylated blue multi-copper oxidase (EC ) Widely abundant in plants, fungi and bacteria atural substrates for laccase: mono-, di-, poly-, and amino-phenols, diamines, lignin Applications: dyeing, detoxification, removal phenolic compounds Redox potentials Fungal laccase: ~ 0.78 V Plant laccase: ~0.43 V June 21, For applications: A. M. Mayer, R. C. Staples, Phytochemistry 60 (2002) 551
13 Extending the potential of Laccase: Mediators C C 2 laccase Mediator CH 2 H 2 H 2 laccase ox Mediator ox C H cinnabarinic acid natural mediator Mediator Yield of ald. (%) ABTS 2 VLA 42-3 S S S ABTS ( V) S 3 - H VLA H (0.92 V) HP 54 HBT 30 TEMP 92 [alc] 20 mm, [med] 30 mol%, 24 h, ph 5, 2, RT, laccase from Trametes Villosa: 150 U/mmol HP (1.08 V) HBT (1.09 V) TEMP (0.75 V) June 21, M. Fabbrini, C. Galli, P. Gentili, J. Mol.Cat. B:Enzym.16 (2002) 231. M. Fabbrini, C. Galli, P. Gentili, D. Machitella, Tet. Lett. 42 (2001) 7551.
![92 V) HP 54 HBT 30 TEMP 92 [alc] 20 mm, [med] 30 mol%, 24 h, ph 5, 2, RT, laccase from Trametes Villosa: 150 U/mmol HP (1.08 V) HBT (1.](/docs-images/45/9352134/images/page_13.jpg "09 V) TEMP (0.75 V) June 21, 2007 13 M. Fabbrini, C. Galli, P. Gentili, J. Mol.Cat. B:Enzym.16 (2002) 231. M. Fabbrini, C. Galli, P. Gentili, D.")
14 Kinetic studies in one phase using water soluble alcohol & TEMP V ini (mm/min) a V ini (mm/min) [S] 0 (mm) a M/S (%m) nitial rate (mm/min) a b c L/S (U/mmol) Effect of substrate (a), TEMP (b) and laccase (c) concentration on the initial rate laccase (47 U/mmol) (120 mm) CH 2 water, ph /2 2 H 2 H + 1/2 H 2 Y.X. Li (10 mol%) June 21, Arends et al. Biocatal. & Biotransform. 24 (2006) 443.
15 xidation of Linear Aliphatic Hydrophobic Alcohols RCH 2 laccase/temp 2, 30 C RCH Long-chain Allylic Conversion % after 4h after 7h 20 0 Heptanol ctanol onanol Decanol Undecanol Dodecanol Geraniol Citronellol June 21, Reaction conditions: 1.6 mmol substrate, Lacc/Subs: 62.5 U/mmol, TEMP/Subs:9.4 mol%, 0.1 M phosphate buffer (ph 4) 2-cten-1-ol nga Matijosyte
16 xidation of Aromatic Alcohols RCH 2 laccase/temp 2, 30 C RCH Substrate Product Conversion % after 4 hour 3-Methoxybenzyl alcohol Veratryl alcohol 4-Methoxybenzyl alcohol 3-Phenyl-2-propene-1-ol 3-(Hydroxymethyl) pyridine Benzyl alcohol 3-Methoxybenzaldehyde 100 3,4-Dimethoxybenzaldehyde Methoxybenzaldehyde 98 Cinnamaldehyde 72 icotinaldehyde 98 Benzaldehyde 90 June 21, Reaction conditions: 1.6 mmol substrate, Lacc/Subs: 62.5 U/mmol, TEMP/Subs:9.4 mol%, 0.1 M phosphate buffer (ph 4)
17 xidation of Secondary Alcohols RR 1 CH laccase/temp 2, 30 C RR 1 C= Substrate Product Conversion % after 4 hour 2-ctanol 3-ctanol 1-Phenylethanol Cyclohexanol 2-ctanone 0 3-ctanone 0 Acetophenone 34 Cyclohexanone 16 June 21, Reaction conditions: 1.6 mmol substrate, Lacc/Subs:62.5 U/mmol, TEMP/Subs:9.4 mol%, 0.1 M phosphate buffer (ph 4)
18 Mechanism involves xoammonium ions R 1 R 2 H + + H + R 1 R 2 June 21, Arends et al. Tetrahedron 62 (2006) 6659.
19 Tempo Catalysed xidation of Alcohols in Chemistry R 1 TEMP (1 m%) R 1 abr (10 m%) + acl + acl + H 2 H CH R 2 Cl 2, H 2, 0 C 2 R 2 < 10 min Primary > Secondary Anelli protocol Cl 2 /Br 2 Cl - Br R 1 R 2 H Cl - Br - R 1 + H2 R 2 June 21, P.L. Anelli, C. Biffi, F. Montanari, S. Quici, J. rg. Chem 52 (1987) 2559.
20 Laccase June 21, T. Bertrand, C. Jolivalt, P. Briozzo, E. Caminade,. Joly, C. Madzak and C. Mougin, Biochemistry 23 (2002) Trametes Versicolor
21 EPR results demonstrate: direct oxidation of TEMP by the laccase enzyme a b (a) Laccase + 44µM TEMP (= 1 eq) (b) Laccase + 3 eq TEMP c (c) Laccase + 13 eq TEMP. d (d) Laccase + 13 eq TEMP after exposure to oxygen Magnetic field (Gauss) X-band EPR spectra of laccase and TEMP June 21,
22 Postulated Mechanism R R 1 R 2 R 2 H 2 Laccase(Cu+) Laccase(Cu2+) + R R - + H R 1 R 2 H R 1 R 2 June 21,
23 mportant application: Laccase-TEMP catalyzed oxidation of sugar derivatives Ac CH 2 Ac n TEMP (9 mol%), 2 Laccase from Trametes pubescens (272 U/mmol); ph 4.5, 48 h Ac C Ac n S. Riva et al. Green Chem. 7 (2005) 310 See also: L. Viikari et al. (1999) W ; J.M. Jetten et al. (2000) W 00/50621 Better results using laccase-clea; CLEA Technologies; T June 21,
24 Take Home message Laccase for green oxidations of primary alcohols June 21,
25 Acknowledgements Dr. Yu-Xin Li nga Matijosyte, MSc Rolf van der Kooij Aleksandra Miernowska, MSc Prof. R.A. Sheldon Prof. W.R. Hagen Prof. S. de Vries Collaborations Dr. Patrick Gamez; Prof. J. Reedijk Dr. K. Kervinen; Prof. B. Weckhuysen Financial Contributions ACTS/BS; B-Basic; RSC-Catalysis; Avantium Technologies, P-catalysis; CST-D29 June 21,
26 June 21,
27 3 rd nternational Conference on Green and Sustainable Chemistry 1-5 July 2007 / Delft / The etherlands rganized by : Department of Biotechnology / Delft University of Technology June 21,
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