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Bioorganic Chemistry

Complex organic synthesis based on biological & chemoenzymatic strategies
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Head of the Research Group: Prof. Jan Deska

As one of the core disciplines within the chemical sciences, organic chemistry provides the enabling tools for today's chemical industry to address pivotal societal challenges by means of pharmaceutical and agrochemical technologies. Here, the implementation of biological instruments, arising from the enormous progress in modern biotechnology in recent years, offers new opportunities en route to improved synthetic strategies with regard to selectivity, resource-efficiency and cascade design. Combining techniques of contemporary organic chemistry, catalysis and biotechnology, our group provides the interdisciplinary environment to tackle the challenges of modern synthesis from the basic method development to applications in the preparation of natural products.

List of most recent publications. (research.aalto.fi)

Reversed Biomimetics

Nature has always been inspirational to chemists in their development of novel methodologies and particularly in the design of catalytic entities both in organo- and metal catalysis. On the other hand, numerous entirely abiotic and extremely powerful chemical transformations were created over the past two centuries and today, the synthetic chemist's toolbox heavily relies on this heritage. Envisioning bio-based production platforms, it appears pivotal to broaden the biological reaction portfolio towards chemically relevant transformations that might not be natural at first glance, hence lacking the requisite enzymatic machinery.

In the past few years, we could show that even wild-type enzymes, particularly oxidoreductases, are able to engage in substrate activations beyond their original tasks and therby catalyze completely unnatural reactions such as the oxygenative Achmatowicz ring enlargement of furfuryl alcohols (see Scheme 1) as well as redoxisomerizations, Alder-ene reactions and carbene transfer processes [1,2].

Scheme 1. Biocatalytic interpretation of a non-natural synthetic transformation.

With the identification of these new biological tools, the construction of enzymatic cascades featuring unnatural modules becomes feasible and will be exploited in our future research efforts towards integrated biocatalytic synthesis strategies and novel cellular factories.

Chemoenzymatic Total Synthesis

In addition to fully biocatalytic scenarios, also the combination of chemocatalysis and enzymatics can be used in a very beneficial manner when it comes to the synthesis of complex molecules. While enzymatic protocols are often limited by a somewhat narrow substrate scope, strategies that allow for metal-mediated follow-up transformations as part of multicatalytic synthetic cascades as exemplified in the total syntheses of e.g. the hyperiones [3,4] or osmundalactone [5].

​​​​​​​Bioinspired and Biocoupled Hydrogen Production

Beyond the well-explored utility of biocatalysts in the synthesis of complex molecules, enzyme-driven approaches can also serve as effective alternatives to the current purely metal-based state-of-the-art catalysts in small molecule activation. In a first proof-of-concept study, we demonstrated the power of bioinspired strategies by intercepting the natural methanol activation pathway of methylotrophic organisms exploiting alcohol oxidases in combination with a formaldehyde-specific ruthenium complex yielding a hydrogen production system for the methanol reforming at substantially reduced reaction temperatures compared to transition metal-based catalysts.[6,7]

Biography

Prof. Jan Deska was born on May 27, 1979 in Quierschied, Germany. He received his diploma in Chemistry (2004) and his Dr. rer. nat. (2007) from Saarland University, Germany under supervision of Prof. Uli Kazmaier (topic: novel methods for metal-mediated peptide backbone modifications). From 2007 to 2010, he conducted postdoctoral studies in the groups of Prof. Goverdhan Mehta (IISc Bangalore, India, topic: total synthesis of phaeofuran A) and Prof. Jan-E. Bäckvall (Stockholm University, Sweden, topic: dynamic-kinetic resolution of axially chiral allenes). In 2010, Deska joined Cologne University, Germany, as Liebig junior group leader establishing his independent research in the field of Synthetic Biocatalysis. Additionally, in 2014/2015, he held the position of teaching substitute professor (chair for Organic Chemistry I) at RWTH Aachen University, Germany. In August 2015, Deska was appointed as Associate Professor to Aalto University where he is currently heading the research group of Synthetic Organic Chemistry.