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Organic Synthesis

Our research involves the introduction of molecular biology into synthetic organic chemistry in the quest to exploit directed evolution of stereoselective enzymes as catalysts in asymmetric reactions. The goals include the implementation of efficient molecular biological strategies and techniques for probing protein sequence space rapidly and the development of high-throughput screening systems for evaluating stereoselectivity and thermostability of enzyme mutants. Current challenges include selective C-C and C-H activating oxidations of simple and complex organic compounds as well as hydrolytic processes.

 

 

Manfred T. Reetz (Emeritus)

Prof. Dr. Dr. h.c. Manfred T. Reetz (Emeritus)

2011
Starting September 1 Emeritus-Status and Hans-Meerwein-Research-Professor at Philipps-Universität Marburg as external Group Leader of the Max-Planck-Institute
1993–2011
Chairman of the Studiengesellschaft Kohle mbH, SGK (Patent Department of the Institute)
1993–2002
Managing Director of the Max-Planck-Institut für Kohlenforschung
1992–2010
Honorary Professor at Ruhr-Universität Bochum
1991–2011
Director at the Max-Planck-Institut für Kohlenforschung
1989–1990
Guest Professor at Florida State University/USA
1980–1991
Full Professor at University of Marburg
1978–1980
Associate Professor at University of Bonn
1978
Guest Professor at University of Wisconsin/USA
1972–1978
Assistant Professor (Habilitand/Dozent) at University of Marburg
1971–1972
Post-Doc with R. W. Hoffmann at University of Marburg
1969
Doctoral degree, University of Göttingen with U. Schöllkopf
1967
Master degree, University of Michigan, Ann Arbor/USA
1965
Bachelor degree, Washington University, St. Louis/USA
1952
Immigration to the USA
1943
Born August 13, 1943 in Hirschberg/Germany
2011
Otto Hahn Prize (Germany)
2011
Tetrahedron Prize for Creativity in Organic Chemistry
2009
Yamada-Koga Prize (Japan)
2009
Arthur C. Cope Award, ACS (USA)
2009
Lilly Distinguished Lectureship Award
2007
Ruhr Prize for Arts and Science (Germany)
2007
Honorary Professor at Shanghai Institute of Organic Chemistry (China)
2006
Prelog Medal (Switzerland)
2006
Ernst Hellmut Vits-Prize (Germany)
2005–
Foreign Member of the Royal Netherlands Academy of Arts and Sciences
2005
Karl Ziegler Prize (German Chemical Society)
2005
Cliff S. Hamilton Award in Organic Chemistry (USA)
2003
Centenary Lecture Award (UK)
2003
Hans Herloff Inhoffen Medal (Germany)
2001–
Member of the Academy of Sciences of the State of NRW
2000
Nagoya Gold Medal of Organic Chemistry (Japan)
1997–
Member of the German Academy of Sciences Leopoldina
1997
Fluka Prize "Reagent of the Year 1997"
1992–2010
Honorary Professsor at Ruhr-Universität Bochum
1989
Leibniz Prize of the German Research Council (DFG)
1986
Otto Bayer Prize (Germany)
1978
Chemistry Prize of the Academy of Sciences Göttingen
1977
Jacobus van't Hoff Award Grant (The Netherlands)
1976
German Chemical Industries Prize (Dozentenstipendium des FCI)
2010–
Member of the Advisory Board of the Karl-Ziegler-Foundation
2009–2010
Coordinator of ORCHEM 2010
2009–2010
President of BOSS12
2009–
Associate Editor of Chemistry and Biology
2007–2011
Senator of the German Academy of Sciences Leopoldina (Chemistry Section)
2007–2008
Member of Research Assessment Exercise, RAE (Evaluation of UK Chemistry Departments)
2006–2007
Member of the International Advisory Board of the Chemistry Department of Nagoya University (Japan)
2006–
Member of the Advisory Board "Topics in Stereochemistry", John Wiley & Sons
2005–
Member of the Editorial Advisory Board "Bulletin of the Chemical Society of Japan"
2003–
Member of the Board of Governors of the Alfried Krupp von Bohlen und Halbach-Foundation
2003–
Member of the Advisory Board of "QSAR & Combinatorial Science", Wiley-VCH
2002–2010
Member of the Editorial Board "Angewandte Chemie", Wiley-VCH
2001–2005
Member of Scientific Advisory Board for the School of Engineering and Science, International University Bremen
2000–2005
Member of Advisory Board, "Advanced Synthesis and Catalysis", Wiley-VCH
2000–
Member of Advisory Board, "Russian Journal of Organic Chemistry"
1999–
Member of Selction Committee, Alfried Krupp-Prize
1999–2008
Member of the Advisory Board, Catalysis NRSC (The Netherlands)
1999–2005
Chairman of Selection Committee, Adolf-von-Bayer-Prize (GDCh)
1998–2005
Member of Advisory Board, Emil-Fischer-Prize (GDCh)
1997–
Member of Editorial Board, "Topics in Organometallic Chemistry", Spinger
1997–2000
Member of Board, Catalysis Network (Katalyseverbund) NRW
1997
President of Bürgenstock-Conference
1995
Vice-President of German Chemical Society (GDCh)
1994–2001
Memberof the Selection Committee, Karl Heinz Beckurts-Prize
1994–1999
Member of Advisory Borad, "Nachrichten aus Chemie, Technik und Laboratorium"
1994–1998
Member of Selection Committe, Carl-Duisberg-Prize (GDCh)
1993–2001
Member of the Scientific Advisory Board, Institut für Organische Katalyseforschung Rostock (Germany)
1992–1996
Chairman of Selection Committee, August-Wilhelm-von-Hofmann-Prize (Medal, GDCh)
1990–1995
Member of the Board, German Chemical Society (GDCh)
1989–1992
Committee Member of Fonds der Chemischen Industrie (engeres Kuratorium)
1987–1988
Chairman of Chemistry Department, University Marburg (Germany)
Publications 2014

S. Hoebenreich, F. E. Zilly, C. G. Acevedo Rocha, M. Zilly, M. T. Reetz
Speeding up Directed Evolution: Combining the Advantages of Solid-Phase
Combinatorial Gene Synthesis with Statistically Guided Reduction of Screening Effort.
ACS Synth. Biol. 2014; DOI: 10.1021/sb5002399.
        

M. T. Reetz
One Hundred Years of the Max‐Planck‐Institut für Kohlenforschung.
Angew. Chem. 2014, DOI: 10.1002/ange.201403217.
Angew. Chem. Int. Ed. 2014, DOI: 10.1002/anie.201403217.

A. Ilie, M. T. Reetz,
Directed Evolution of Artificial Metalloenzymes.
Isr. J. Chem. 2014, accepted.

C. G. Acevedo-Rocha, R. Agudo, M. T. Reetz
Directed evolution of stereoselective enzymes based on genetic selection as opposed to
screening systems.
J. Biotechnol. 2014; DOI: 10.1016/j.jbiotec.2014.04.009.

G.-D. Roiban, R. Agudo, M. T. Reetz
Cytochrome P450 Catalyzed Oxidative Hydroxylation of Achiral Organic Compounds with
Simultaneous Creation of Two Chirality Centers in a Single C-H Activation Step.
Angew. Chem. 2014, DOI; 10.1002/ange.201310892.
Angew. Chem. Int. Ed. 2014; DOI: 10.1002/anie.201310892.

P. Tielmann, H. Kierkels, A. Zonta, A. Ilie, M. T. Reetz
Increasing the activity and enantioselectivity of lipases by sol–gel immobilization: further
advancements of practical interest
.
Nanoscale 2014, 6, 6220-6228.

G.-D. Roiban, A. Ilie, M. T. Reetz
The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes.
Chem. Lett. 2014, 43, 2–10.

G.-D. Roiban, G. Mehler, M. T. Reetz
Palladium-Catalysed Amination of Aryl- and Heteroaryl Halides Using tert-Butyl
Tetraisopropylphosphorodiamidite as an Easily Accessible and Air-Stable Ligand.
Eur. J. Org. Chem. 2014, 2070-2076.

C. G. Acevedo-Rocha, S. Kille, M. T. Reetz
Iterative Saturation Mutagenesis: A Powerful Approach to Engineer Proteins by
Simulating Darwinian Evolution.
In: Directed Evolution Library Creation: Methods and Protocols, 2nd Edition
(Eds.: D. Ackerley, J. Copp, E. Gillam)
Methods in Molecular Biology
Humana Press, Totowa, 2014; DOI 10.1007/978-1-4939-1053-3_7

C. G. Acevedo-Rocha, M. T. Reetz
Assembly of Designed Oligonucleotides: A Useful Tool in Synthetic Biology for
Creating High Quality Combinatorial DNA Libraries.
In: Directed Evolution Library Creation: Methods and Protocols, 2nd Edition
(Eds.: D. Ackerley, J. Copp, E. Gillam)
Methods in Molecular Biology
Humana Press, Totowa, 2014, DOI: 10.1007/978-1-4939-1053-3_13.

Publications 2013

R. Agudo, G.-D. Roiban, M. T. Reetz
Induced Axial Chirality in Biocatalytic Asymmetric Ketone Reduction.
J. Am. Chem. Soc. 2013, 135, 1665-1668.
doi/abs/10.1021/ja3092517

S. Kille, C. G. Acevedo-Rocha, L. P. Parra, Z.-G. Zhang, J. J. Opperman, M. T. Reetz,
J. P. Acevedo
Reducing Codon Redundancy and Screening Effort of Combinatorial Protein Libraries Created by Saturation Mutagenesis.
ACS Synth. Biol. 2013, 2, 83-92.
doi/abs/10.1021/sb300037w

M. T. Reetz
Die Bedeutung von Additiven und Nicht-Additiven Mutationseffekten im Protein-Engineering.
Angew. Chem. 2013, 125, 2720-2729.
The Importance of Additive and Non-Additive Mutational Effects in Protein Engineering.
Angew. Chem. Int. Ed. 2013, 52, 2658-2666. 53
/doi/10.1002/anie.201207842

Q. Wu, P. Soni, M. T. Reetz
Laboratory Evolution of Enantiocomplementary Candida Antarctica Lipase B Mutants with Broad Substrate Scope.
J. Am. Chem. Soc. 2013, 135, 1872-1881.
doi/abs/10.1021/ja310455t

G.-D. Roiban, M. T. Reetz
Enzympromiskuität: Ein P450-Enzym als Carbentransferkatalysator.
Angew. Chem. 2013, 125, 5549-5550.
Enzyme Promiscuity: Using a P450 Enzyme as a Carbene Transfer Catalyst.
Angew. Chem.Int. Ed. 2013, 52, 5439-5440.
doi/10.1002/anie.201301083

Z.-G. Zhang, G.-D. Roiban, J. P. Acevedo, I. Polyak, M. T. Reetz
A New Type of Stereoselectivity in Baeyer-Villiger Reactions: Access to E- and Z-Olefins.
Adv. Synth. Catal. 2013, 355, 99-106.
doi/10.1002/adsc.201200759

M. T. Reetz
Practical Protocols for Lipase Immobilization Via Sol-Gel Techiques.
In: Methods in Biotechnology, Vol. 1051 (Immobilization of Enzymes and Cells), (Ed.: J. M. Guisan), 2. Edition, Humana Press: Totowa, 2013, pp. 241-254.

L. P. Parra, R. Agudo, M. T. Reetz
Directed Evolution Using Iterative Saturation Mutagenesis Based on Multi-Residue Sites
ChemBioChem 2013;
DOI: 10.1002/cbic.201300486.

W. Augustyniak, H. Wienk, R. Boelens, M. T. Reetz
1H, 13C and 15N resonance assignments of wild-type Bacillus subtilis Lipase A and its mutant evolved towards thermostability.
Biomol. NMR Assign. 2013, 7, 249-252.
10.1007/s12104-012-9420-z

M. T. Reetz
Biocatalysis in organic chemistry and biotechnology: Past, present, and future.
J. Am. Chem. Soc. 2013, 135, 12480-12496.
doi/abs/10.1021/ja405051f

I. Polyak, M. T. Reetz, W. Thiel
Quantum mechanical/molecular mechanical study on the enantioselectivity of the enzymatic baeyer-villiger reaction of 4-hydroxycyclohexanone.
J. Phys. Chem. B, 2013, 117, 4993-5001.
doi/abs/10.1021/jp4018019

G.-D. Roiban, R. Agudo, M. T. Reetz
Stereo- and regioselectivity in the P450-catalyzed oxidative tandem
difunctionalization of 1-methylcyclohexene.
Tetrahedron, 2013, 69, 5306-5311.

C. G. Acevedo-Rocha, M. T. Reetz
Assembly of Designed Oligonucleotides: A Useful Tool in Synthetic Biology for
Creating High Quality Combinatorial DNA Libraries.
In: Directed Evolution Library Creation: Methods and Protocols, 2nd Edition
(Eds.: D. Ackerley, J. Copp, E. Gillam)
Methods in Molecular Biology
Humana Press, Totowa, 2013, in press.

C. G. Acevedo-Rocha, S. Kille, M. T. Reetz
Iterative Saturation Mutagenesis: A Powerful Approach to Engineer Proteins by
Simulating Darwinian Evolution. 54
In: Directed Evolution Library Creation: Methods and Protocols, 2nd Edition
(Eds.: D. Ackerley, J. Copp, E. Gillam)
Methods in Molecular Biology
Humana Press, Totowa, 2013, in press.

S. Kille, M. T. Reetz
Protein Engineering: Development of Novel Enzymes for the Improved Reduction of C=C Double Bonds.
In: Synthetic Methods for Biologically Active Molecules-Exploiting the Potential of Bioreductions.
(Ed.: E. Brenna)
Wiley-VCH, Weinheim, 2013.

R. Agudo, M. T. Reetz
Designer Cells for Stereocomplementary De Novo Enzymatic Cascade Reactions
Based on Laboratory Evolution.
Chem. Comm. 2013, 49, 10914-10916.
/cc/c3cc46229c

L. P. Parra, R. Agudo, M. T. Reetz
Directed Evolution by Using Iterative Saturation Mutagenesis Based on Multiresidue Sites
ChemBioChem 2013, 14, 2301-2309.
doi/10.1002/cbic.201300486

Publications 2012

M. T. Reetz
Artificial Metalloenzymes as Catalysts in Stereoselective Diels-Alder Reactions.
Chem. Rec. 2012, 12, 391-406.
http://dx.doi.org/10.1002/tcr.201100043

W. Augustyniak, H. Wienk, R. Boelens,  M. T. Reetz
1H, 13C and 15N resonance assignment of wild-type Bacillus subtilis Lipase A and its mutant evolved towards thermostability.
Biomol. NMR Assignemnts 2012, DOI: 10.1007/s12104-012-9420-z.

 Z.-G. Zhang, L. P. Parra, M. T. Reetz
Protein Engineering of Stereoselective Baeyer-Villiger Monooxygenases.
Chem. Eur. J. 2012, 18, 10160-10172.
http://dx.doi.org/10.1002/chem.201202163

S. Cesarini, C. Bofill, F. I. J. Pastor, M. T. Reetz, P. Diaz
A thermostable variant of P. aeruginosa cold-adapted LipC obtained by rational design and saturation mutagenesis.
Process Biocgem. 2012, 47, 2064-2071.
http://dx.doi.org/10.1002/chem.201202163

M. T. Reetz
Laboratory evolution of stereoselective enzymes as a means to expand the toolbox of organic chemists.
Tetrahedron 2012, 68, 7530-7548.
http://dx.doi.org/10..1016/j.tet.2012.05.093

S. Kille, C. G. Acevedo-Rocha, L. P. Parra, Z.-G. Zhang, D. J. Opperman, M. T. Reetz,
J. P. Acevedo
Reducing Codon Redundancy and Screening Effort of Combinatorial Protein Libraries Created by Saturation Mutagenesis
ACS Synth. Biol. 2012, DOI: 10.1021/sb300037w.

R. Agudo, G.-D. Roiban, M. T. Reetz
Achieving Regio- and Enantioselectivity of P450-Catalyzed Oxidative CH Activation of Small Functionalized Molecules by Structure-Guided Directed Evolution.
ChemBioChem 2012, 13, 1465-1473.
http://dx.doi.org/10.1002/cbic.201200244

C. G. Acevedo-Rocha, M. T. Reetz
Tuning lipase activity with perfluoro carboxylic acids as additives.
Catal. Sci. Technol. 2012, 2, 1553-1555.
http://dx.doi.org/10.1039/C2CY20173A

Y. Gumulya, J. Sanchis, M. T. Reetz
Many Pathways in Laboratory Evolution Can Lead to Improved Enzymes: How to Escape from Local.
ChemBioChem 2012, 13, 1060.1066.
http://dx.doi.org/10.1002/cbic.201100784

I. Polyak, M. T. Reetz, W. Thiel
Quantum Mechanical/Molecular Mechanical Study on the Mechanism of the Enzymatic
Baeyer-Volliger Reaction.
J. Am. Chem. Soc. 2012, 134, 2732-2741.
http://dx.doi.org/10.1021/ja2103839

X. Feng, J. Sanchis, M. T. Reetz, H. Rabitz
Enhancing the Efficiency of Directed Evolution in Focused Enzyme Libraries by the Adaptive Substituent Reordring Algorithm.
Chem.-Eur. J. 2012, 18, 5646-5654.
http://dx.doi.org/10.1002/chem.201103811

M. T. Reetz
Directed Evolution of Enzymes.
In: Enzyme Catalysis in Organic Synthesis, 3. Edition, Vol. 1-3,
(Eds. K. Drauz, H. Gröger, O. May),
Wiley-VCH, Weinheim, 2012 Vol.1, pp. 119-190.

W. Augustyniak, A. A. Brzezinska, T. Pijning, H. Wienk, R. Boelens,
B. W. Dijkstra, M. T. Reetz
Biophysical characterization of mutants of Bacillus subtilis lipase evolved for thermostability: Factors contributing to increased activity retention.
Protein Sci. 2012, 21, 487-497.
http://dx.doi.org/10.1002/pro.2031

 

1. Manfred T. Reetz was chosen to be the first Hans-Meerwein-Research-Professor at Philipps-University in Marburg. 
Following the termination of his contract as Director at the Max-Planck-Institut für Kohlenforschung at the age of 68 years, Manfred T. Reetz has moved to the Philipps-University in Marburg, where he was recently elected to become the first Hans-Meerwein-Research-Professor. At his new site he directs a group of six coworkers, financed by a special fund of the Max-Planck-Society and the Mülheim MPI. Thus, he has two appointments, namely external (emeritus) group leader of the MPI für Kohlenforschung and member of the Marburg chemistry faculty.

2. Paper by Reetz group selected by Faculty 1000 as top contribution.
The post-publication peer review organization Faculty 1000 has evaluated and selected the recent publication of the Reetz group regarding "Regio- and stereoselectivity of P450-cataysed hydroxylation of steroids by laboratory evolution" (S. Kille, F. E. Zilly, J. P. Acevedo, M. T. Reetz, Nature Chem. 2011, 3, 738-743). Election of a publication to F1000 places the work of the "top 2% of published articles in biology and medicine".

3. Manfred T. Reetz has been selected to receive the Otto-Hahn-Prize for his seminal contributions to methodology development in synthetic organic chemistry, especially for his concept of directed evolution of stereoselective enzymes as catalysts in asymmetric transformations. The € 50,000 endowed prize, initiated in 2005, is awarded every two years by the German Chemical Society (GDCh), The German Physics Society (DPG) and the city of Frankfurt/Main (the birthplace of Otto-Hahn). Past winners are Theodor Hänsch (physics/2005), Gerhard Ertl (chemistry/2007) and Stefan Hell (physics/2009). The ceremony took place on November 22, 2011 in the historic Paulskirche in Frankfurt/Main.

4. Manfred T. Reetz has been selected to receive another prestigious award, namely the international Tetrahedron Prize for Creativity in Organic Chemistry 2011, endowed with $10,000.

Research Topics

Directed evolution of enantioselective and thermostable enzymes

Organic Synthesis in the Reetz Group

Enzymes have been used as catalysts in organic chemistry and in biotechnology for more than 100 years, but broad application has never been achieved due to a number of traditional limitations which often include limited substrate scope, poor stereoselectivity and/or insufficient stability. The molecular biological methods of directed evolution offer a way out of this dilemma. Indeed, some time ago we introduced a fundamentally new approach to asymmetric catalysis, namely laboratory evolution of stereoselective enzymes as catalysts in synthetic organic chemistry. Recent methodology development in our lab culminated in iterative saturation mutagenesis, which allows us to address stereoselectivity, substrate scope and thermostability with unprecedented efficiency.

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Organic Synthesis in the Reetz Group

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  • Dr. Juan Pablo Acevedo-Cox

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  • Dr. Rubén Agudo Torres

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  •  Ellen Enk

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  • Dr. Sabrina Kille

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  • Dr. Loreto P. Parra

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  • Dr. Pamela Tores Salas

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