LBB-WUT crew with publication in ACS Catalysis

Our group, with the leading contribution of our Ph.D. students (Aleksandra Rudzka and Natalia Antos) and in collaboration with scientists from Prof. Wolfgang Kroutil’s group (the „Elk Crew”, the University in Graz, Austria), published a research article on the novel photo-biocatalytic method of deracemization of secondary alcohols using visible light and recombinant alcohol dehydrogenases.

In the published work, we proved that the combination of both catalytic processes, i.e., photooxidation of racemic alcohols in the presence of 9-fluorenone in DMSO irradiated with blue light (440 nm) and bio-transhydrogenation of the resulting ketones using the enzymes mentioned above, in a sequential one-pot/two-step procedure, enables the synthesis of optically active alcohols in high yield (>90%) and excellent enantiomeric excess (>99%). It is worth mentioning that the newly developed asymmetric photo-biocatalytic method is efficient toward a broad substrate scope, while the obtained products of these transformations are chiral building blocks useful for the synthesis of valuable pharmaceuticals.

In addition, research on photo-biocatalytic cascade processes has led to a breakthrough discovery; namely, scientists from the LBB WUT have demonstrated that recombinant E. coli cells harboring alcohol dehydrogenases from Rhodococcus ruber (E. coli/ADH-A) and Lactobacillus kefir (E. coli/Lk-ADH) show unexpectedly high catalytic activity and stereoselectivity despite the strongly acidic pH (1.5-2.2) of the crude reaction mixture obtained after photooxidation of racemic substrates. The rationalization of this rather unprecedented phenomenon was supported by numerous validation experiments and their detailed analysis, providing the basis for a hypothetical mechanism for the formation of sulfur compounds with potential modulating properties against the enzymes, as mentioned above. The results of the conducted research may contribute to the initiation of new applications in bioorganic chemistry and biotechnology and play a key role in planning stereocontrolled syntheses of enantiomerically enriched high-added value products from chiral alcohols.

Work on the impact of this effect on other classes of enzymes (i.e., transaminases), including verification of the scope of applicability of the developed method toward new substrates, is currently the basis of intensive research conducted by Dr. Borowiecki’s group. Taking advantage of this fact, we warmly invite all students interested in this research topic to cooperate with us to carry out similar scientific projects as part of their future engineering and/or M.Sc thesis.

The results of the study are described in a paper entitled: „One-Pot Sequential Two-Step Photo-Biocatalytic Deracemization of sec-Alcohols Combining Photocatalytic Oxidation and Bioreduction„ and published in the very prestigious catalytic journal ACS Catalysis (ISSN: 2155-5435; IF: 13.7).

The article was written in tribute to Prof. Krzysztof Schmidt-Szałowski (1930-2023) and Prof. Przemysław Szczeciński (1946-2023), who passed away last year.

The research published in this paper was funded by the National Science Center (NCN) under the grant „OPUS 24” (No. 2022/47/B/ST4/00139)

More information can be found on the journal’s website: https://pubs.acs.org/doi/10.1021/acscatal.3c05100.

(date: 10.02.2024)

LBB-WUT crew with publication in Communications Chemistry

Our lab team together with colleagues from Austria (an „Elk Crew” headed by Prof. Wolfgang Kroutil form University of Graz) have characterized a novel biocatalyst for the asymmetric transhydrogenation of carbonyl compounds. The title biocatalyst (named Lk-ADH Prince) is a variant of alcohol dehydrogenase from Lactobacillus kefir and was prepared using a site saturation mutagenesis strategy.

In the published work, we proved that Lk-ADH Prince exhibits excellent catalytic properties, including high activity and stereoselectivity towards a wide range of ketones, which asymmetric biotransformation products are the key chiral building blocks useful in the synthesis of pharmaceuticals. Studies of the catalytic properties were also rationalized using molecular docking simulations and detailed analysis of the morphology of the tunnels leading to the enzyme’s active site.

The results were published in Communications Chemistry (ISSN: 2399-3669, IF: 5.9) and are entitled „Biocatalytic characterization of an alcohol dehydrogenase variant deduced from Lactobacillus kefir in asymmetric hydrogen transfer„.

The research published in this paper was funded by the National Science Center (NCN) under the grant „OPUS 24” (No. 2022/47/B/ST4/00139).

More information can be found on the journal’s website: https://www.nature.com/articles/s42004-023-01013-1?utm_source=rct_congratemailt&utm_medium=email&utm_campaign=oa_20231012&utm_content=10.1038/s42004-023-01013-1#Sec22

(date: 12.10.2023)

Dr. Paweł Borowiecki became a member of the European Society of Applied Biocatalysis (ESAB)

We want to inform you that Dr. Borowiecki has been invited to join the elite group of members of the ESAB – European Society of Applied Biocatalysis.

ESAB is an organization of professional biotechnologists from all over Europe, dedicated to developing and promoting Industrial Biotechnology (so-called White Biotechnology) among employees of academia, research institutes, and the industrial sector.

ESAB is involved in organizing scientific conferences, webinars, and educational workshops.

ESAB cooperates with the European Technology Platform for Sustainable Chemistry (SusChem), a public-private partnership organization established by the European Commission to increase investment in research and innovation and enhance European competitiveness in various biotechnology sectors, including but not limited to pharmaceuticals, agrochemicals, cosmetics, food, fuel, energy, textiles, etc.

(date: 21.07.2023)

LBB-WUT crew published a new paper in The Journal of Organic Chemistry

We are delighted to announce that the publication entitled: „Chemoenzymatic synthesis of tenofovir” has been published in The Journal of Organic Chemistry (ISSN: 0022-3263, IF: 3,6).

This article reports on novel chemoenzymatic routes toward tenofovir (an anti-HIV active pharmaceutical ingredient) using low-cost starting materials and commercial or homemade enzyme preparations as biocatalysts. The biocatalytic key step was accomplished either via stereoselective reduction of the respective ketones using alcohol dehydrogenases or via kinetic resolution of the corresponding racemic alcohols using lipases.

This work is another excellent example of the fruitful collaboration of Dr. Borowiecki’s research group with Prof. Wolfgang Kroutil from the University of Graz (Austria).

These studies were funded by the National Science Center (NCN) of Poland in the framework of the „SONATA 15” grant (No. 2019/35/D/ST4/01556).

For more information, see the journal’s official website:

https://pubs.acs.org/doi/10.1021/acs.joc.3c01005

(date: 20.07.2023)

LBB-WUT crew published a new paper in Pharmaceutics

We are pleased to announce that the manuscript of scientists from our Chair, entitled: „Synthesis and Anticancer Activity of Novel Dual Inhibitors of Human Protein Kinases CK2 and PIM-1” has been published in Pharmaceutics (ISSN: 1999-4923, IF: 5.4).

The published paper reports on the development and synthesis of novel polybrominated benzoazoles and their inhibitory activity toward CK2 and PIM-1 protein kinases. Concomitantly with the inhibition studies toward recombinant enzymes, the influence of the obtained compounds on the viability of three human carcinoma cell lines, i.e., acute lymphoblastic leukemia (CCRF-CEM), human chronic myelogenous leukemia (K-562), and breast cancer (MCF-7), as well as non-cancerous cells (Vero), was evaluated.

Noteworthy, among the newly developed dual inhibitors, 1,1,1-trifluoro-3-[(4,5,6,7-tetrabromo-1H-benzimidazol-2-yl)amino]propan-2-ol demonstrates the highest selectivity and the most prominent proapoptotic properties towards the studied cancer cells, especially towards acute lymphoblastic leukemia, in addition to inducing autophagy in K-562 cells.

The article was dedicated to Prof. Zygmunt Kazimierczuk (1945-2021) – one of the most recognized Polish bioorganic chemists, who dedicated the last two decades of his life to the development and synthesis of inhibitors of protein kinases! It is worth mentioning that, thanks to his knowledge and commitment, Professor Kazimierczuk contributed to the production and registration in Poland of an anticancer and immunosuppressive drug available for clinical treatment called biocladribine.

This article belongs to the Special Issue „Kinase Inhibitor for Cancer Therapy„.

For more information, see the journal’s official website: https://www.mdpi.com/1999-4923/15/7/1991

(date: 20.07.2023)

Dr. Borowiecki together with Dr. Zajda and Dr. Matczuk published a new paper in Talanta

We are pleased to announce that the publication entitled: „Effective monitoring of Platinum-DNA adducts formation under simulated physiological conditions by CE-ICP-MS/MS” has been published in Talanta (ISSN: 1873-3573, IF: 6.556).

The article presents the novel approach based on the hyphenation of capillary electrophoresis with inductively coupled plasma tandem mass spectrometry (CE-ICP-MS/MS) for studying Pt-DNA adduct formation. This work is excellent example of cooperation between Dr. Borowiecki and Dr. Joanna Zajda and Dr. Magdalena Matczuk from the Chair of Analytical Chemistry, Faculty of Chemistry, Warsaw University of Technology.

More information about the project can be found at:https://www.sciencedirect.com/science/article/abs/pii/S0039914023005003

(date: 12.06.2023)

Dr. Paweł Borowiecki received funding from NCN Opus 24 grant

The National Science Center (NCN) of Poland has announced the results of the OPUS and SONATA competitions!

The OPUS competition is aimed at all researchers regardless of the stage of their scientific career, while SONATA is aimed at projects carried out by researchers who hold a doctoral degree.

We are pleased to announce that among the winners of the Opus 24 program was Dr. Paweł Borowiecki, who received funding for his scientific project entitled:

„The Power of Hybrid – Development of Novel Multienzymatic Cascade Reactions and Photobiocatalytic Redox Systems for Asymmetric Synthesis of Optically Active Compounds with High Added Value („EnzCasc-Photo4BioCat”)”.

More information about the project can be found at: https://www.ncn.gov.pl/sites/default/files/listy-rankingowe/2022-09-15-opu8jisl/streszczenia/567774-pl.pdf

Congratulations and much success in research work!

(date: 18.05.2023)

Dr. Paweł Borowiecki as a Guest Editor for Special Issue „Chemoenzymatic Synthesis” in Commun. Chem. journal

We are proud to announce that Dr. Borowiecki, together with Dr. Jennifer Bridwell-Rabb from the Department of Chemistry at the University of Michigan, Ann Arbor, and Dr. Sandy Schmidt from the Gröningen Research Institute of Pharmacy, University of Gröningen, will coordinate the edition of a Special Issue entitled: “Chemoenzymatic synthesis” in Nature: Communications Chemistry (ISSN 2399-3669, IF: 7.211).

This Collection aims to present the latest progress in biocatalysis, with topics of interest including but not limited to:

• Enzyme engineering
• Multienzymatic cascades
• Chemoenzymatic cascades
• Metalloenzymes
• Photo-biocatalysis
• Multifunctional biocatalysts
• Enzyme promiscuity

For more details, visit: https://www.nature.com/collections/afjacdgebd/guest-editors

(date: 18.04.2023)

Dr. Paweł Borowiecki became a laureate of the Young PW grant

We are pleased to announce that Dr. Paweł Borowiecki received funding (149 983 PLN; 32 393 EUR) from YOUNG PW (IDUB) grant on his project entitled: “Biotechnological Application of a New Variant of Recombinant Alcohol Dehydrogenase from Lactobacillus kefir in the Asymmetric Synthesis of Optically Active Compounds with High Added Value“.

The YOUNG PW Project aims to support the scientific development of young scientists, i.e., Ph.D. students and employees of the Warsaw University of Technology engaged in scientific activity, who are counted as N-number members and do not have a doctoral degree or have a doctoral degree received less than seven years before the formal grant application.

The research project topics carried out within the framework of the YOUNG PW grant relate to research in the “Strategic Fields of Interaction” field as defined in the “Strategy for the Development of Warsaw University of Technology until 2030”.

(date: 27.03.2023)

Dr. Paweł Borowiecki became a laureate of the „Best of the best of PW” programme

We are pleased to announce that among the winners of the first edition of the „Best of the Best PW” programme was Dr. Paweł Borowiecki.

The aim of this programme is to provide individualized support for outstanding young PW employees in the development of their academic career, both scientific and teaching at WUT.

The program of individualized support for young scientists is funded by the „Excellence Initiative: Research University (IDUB)’.

The list of all winners of the first edition of the „Best of the Best PW” is available at: https://badawcza.pw.edu.pl/Konkursy/Wyniki-konkursow/2023/Wyniki-konkursu-Najlepsi-z-najlepszych-PW

(date: 27.03.2023)

LBB-WUT crew published a new paper in Catalysts

We are pleased to announce that the publication entitled: „Chemoenzymatic Synthesis of Optically Active Alcohols Possessing 1,2,3,4-Tetrahydroquinoline Moiety Employing Lipases or Variants of the Acyltransferase from Mycobacterium smegmatis” has been published in Catalysts (ISSN: 2073-4344, IF: 4.501) and is part of the Special Issue „Applications of Hydrolases in Medicinal Chemistry” hosted by Dr. Borowiecki and Dr. Dominik Koszelewski from the IChO PAS.

The article presents the kinetic resolution of racemic alcohols bearing 1,2,3,4-tetraquinoline substituents using commercially available lipases and the engineered variants of acyltransferase from Mycobacterium smegmatis (MsAcT). Interestingly, the employment of MsAcT variants enabled the separation of the titled enantiomers in an aqueous media, which contradicts the fundamentals of the convenient synthesis of esters due to the unfavorable equilibrium of such reactions in water. This work is another excellent example of fruitful cooperation between Dr. Borowiecki’s team and Prof. Wolfgang Kroutil from the University of Graz.

(date: 12.12.2022)

LBB-WUT crew published a new paper in CrystEngComm

We are pleased to announce that the publication entitled: ‘Supramolecular synthon hierarchy in cyclopropyl-containing peptide-derived compounds’ has been published in CrystEngComm (ISSN: 1466-8033, IF: 3.756).

It is worth noting that this work was carried out in international cooperation with researchers Slovakia and Poland and reports on important aspects of the molecular basis of biological activity of set of novel cyclopropyl-containing peptide-derived compounds, which might be promising candidates for prostate cancer prevention or management. 

(date: 24.11.2022)

LBB-WUT crew published a new paper in the International Journal of Molecular Sciences

We are pleased to announce that the publication entitled: „Chemoenzymatic Synthesis of Optically Active Ethereal Analog of iso-Moramide—A Novel Potentially Powerful Analgesic” has been published International Journal of Molecular Sciences (ISSN: 1422-0067, IF: 6.208).

This article reports on design and synthesize a novel potent analog of iso-moramide utilizing molecular docking calculations and a chemoenzymatic methodology. We also want to inform you that this article has been dedicated in memory of Dr Paul Janssen (1926-2003) who revolutionized medicinal chemistry and human therapies!

These studies were funded by the National Science Center (NCN) of Poland grant „SONATA 15” (Grant No. 2019/35/D/ST4/01556).

(date: 15.10.2022)