Institut für Bioorganische Chemie

New paper by Sebastian Myllek et al. in Org. Biomol. Chem.:
C–N axially chiral carbazoles synthesized via axial-to-axial chirality transfer – up to 91% enantiospecificity! 👏
#AxialChirality #AsymmetricSynthesis #OrganicChemistry #OBCChem #Carbazoles

doi.org/10.1039/D5OB...

Studierende schrieben über Dr. Thomas Classen: „Es gelingt ihm, große Mengen an Lehrstoff übersichtlich zu vermitteln und er unterstützt uns mit Angeboten, die über die eigentliche Vorlesungszeit hinausgehen.“

Unser heutiger Nominierter des #hhuLehrpreis2025: Dr. Thomas Classen aus der Chemie @hhu.de
Studierende schwärmen von der Struktur seiner Veranstaltung und von seinem hohen Engagement. 👏🔬

Herzlichen Dank für die netten Willkommensgrüße @hhu.de 🙂👋

In Chemistry – A European Journal, Marcel Schatton and Mona Haase report the efficient total synthesis of Lansai B via a 6-step chemoenzymatic approach. Congrats to the whole team! 👏
doi.org/10.1002/chem...

#SyntheticChemistry #Biocatalysis #DrugDiscovery #IndoleChemistry #Naturstoffsynthese

We are happy to announce our latest publication in Organic Letters🥳: Application of Cyclic Diaryliodonium Salts in the Synthesis of Axially Chiral Natural Product Analogues | Organic Letters https://pubs.acs.org/doi/full/10.1021/acs.orglett.4c01308

Save the date! April 18, 3 p.m. Thomas Classen will unravel the magic of lupins in his talk (german) "Lupins: Flower magic with green added value" as part of the "Science online" series. #ScienceOnline #Lupins #Sustainability
🔍 More info & access: https://t.co/61mTwl7Mpe

From the Total Synthesis of Semi-Viriditoxin, Semi-Viriditoxic Acid and Dimeric Naphthopyranones to their Biological Activities in Burkitt B Cell Lymphoma - PubMed Dimeric naphthopyranones are known to be biologically active, however, for the corresponding monomeric naphthopyranones this information is still elusive. Here the first enantioselective total synthesis of semi-viriditoxic acid as well as the synthesis of semi-viriditoxin and derivatives is reported …

We are excited to share this new publication 🔥
From the Total Synthesis of Semi-Viriditoxin, Semi-Viriditoxic Acid and Dimeric Naphthopyranones to their Biologica… https://pubmed.ncbi.nlm.nih.gov/38411573/
#OrganicChemistry #naturalcompound

Exciting news! 🎉 Our latest article introduces a cutting-edge method for High-Throughput Colorimetric Detection and Quantification of Indoles and Pyrroloindoles for enzymatic activity determination. Dive into the details here: https://t.co/QHAGyhA3hs
#EnzymeDetection

We are happy to share our new publication: "Application of the C3-Methyltransferase StspM1 for the Synthesis of the Natural Pyrroloindole Motif" | ACS Catalysis https://pubs.acs.org/doi/10.1021/acscatal.3c04952

We are very proud to share this VIP-article:

Atroposelective Total Synthesis of (+)‐Isokotanin A via Combined Metal and Enzyme Catalysis - Christine Ganardi - Advanced Synthesis & Catalysis - Wiley Online Library https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202300698

Moritz Weber developed a new copper ligand as part of his work. Due to its high solubility compared to commercially available ligands it opens up new possibilities to perform “Click”-chemistry. Congrats Moritz! http://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-2034-9427

Pathogen Resistance Depending on Jacalin-Dirigent Chimeric Proteins Is Common among Poaceae but Absent in the Dicot Arabidopsis as Evidenced by Analysis of Homologous Single-Domain Proteins MonocotJRLs are Poaceae-specific two-domain proteins that consist of a jacalin-related lectin (JRL) and a dirigent (DIR) domain which participate in multiple developmental processes, including disease resistance. For OsJAC1, a monocotJRL from rice, it has been confirmed that constitutive expression in transgenic rice or barley plants facilitates broad-spectrum disease resistance. In this process, both domains of OsJAC1 act cooperatively, as evidenced from experiments with artificially separated JRL- or DIR-domain-containing proteins. Interestingly, these chimeric proteins did not evolve in dicotyledonous plants. Instead, proteins with a single JRL domain, multiple JRL domains or JRL domains fused to domains other than DIR domains are present. In this study, we wanted to test if the cooperative function of JRL and DIR proteins leading to pathogen resistance was conserved in the dicotyledonous plant Arabidopsis thaliana. In Arabidopsis, we identified 50 JRL and 24 DIR proteins, respectively, from which seven single-domain JRL and two single-domain DIR candidates were selected. A single-cell transient gene expression assay in barley revealed that specific combinations of the Arabidopsis JRL and DIR candidates reduced the penetration success of barley powdery mildew. Strikingly, one of these pairs, AtJAX1 and AtDIR19, is encoded by genes located next to each other on chromosome one. However, when using natural variation and analyzing Arabidopsis ecotypes that express full-length or truncated versions of AtJAX1, the presence/absence of the full-length AtJAX1 protein could not be correlated with resistance to the powdery mildew fungus Golovinomyces orontii. Furthermore, an analysis of the additional JRL and DIR candidates in a bi-fluorescence complementation assay in Nicotiana benthamiana revealed no direct interaction of these JRL/DIR pairs. Since transgenic Arabidopsis plants expressing OsJAC1-GFP also did not show increased resistance to G. orontii, it was concluded that the resistance mediated by the synergistic activities of DIR and JRL proteins is specific for members of the Poaceae, at least regarding the resistance against powdery mildew. Arabidopsis lacks the essential components of the DIR-JRL-dependent resistance pathway.

Check out our new publication

Pathogen Resistance Depending on Jacalin-Dirigent Chimeric Proteins Is Common among Poaceae but Absent in the Dicot Arabidopsis as Evidenced by Analysis of Homologous Single-Domain Proteins https://www.mdpi.com/2024582 #mdpiplants via @Plants_MDPI

We are very proud to announce our next publication
@ACSCatalysis
Enzymatic C3-Methylation of Indoles Using Methyltransferase PsmD─Crystal Structure, Catalytic Mechanism, and Preparative Applications https://pubs.acs.org/doi/10.1021/acscatal.2c04240#.Y2TKzDFhsY8.twitter

Simple Enzyme Immobilization for Flow Chemistry? An Assessment of Available Strategies for an Acetaldehyde-Dependent Aldolase Enzyme immobilization is a technology that enables (bio-)catalysts to be applied in continuous-flow systems. However, there is a plethora of immobilization methods available with individual advantages and disadvantages. Here, we assessed the influence of simple and readily available methods with respect to the performance of 2-deoxy-d-ribose-5-phosphate aldolase (DERA) in continuous-flow conditions. The investigated immobilization strategies cover the unspecific attachment to carriers via epoxides, affinity-based attachment via metal ion affinity, StrepTag™-StrepTactin™ interaction as well as the covalent affinity attachment of an enzyme to a matrix tethered by the HaloTag®. The metal-ion-affinity-based approach outperformed the other methods in terms of immobilized activity and stability under applied conditions. As most enzymes examined today already have a HisTag for purification purposes, effective immobilization may be applied, as simple as a standard purification, if needed.

Another fresh publication :)

Simple Enzyme Immobilization for Flow Chemistry? An Assessment of Available Strategies for an Acetaldehyde-Dependent Aldolase https://www.mdpi.com/1862730 #mdpimolecules via @Molecules_MDPI

Identification and Characterization of the Haloperoxidase VPO-RR from Rhodoplanes roseus by Genome Mining and Structure-Based Catalytic Site Mapping Halogenating enzymes have evolved in considerable mechanistic diversity. The apparent need for secondary metabolism coincides with the current need to introduce halogens in synthetic products. The potential of halogenating enzymes and, especially, vanadate-dependent haloperoxidases has been insufficiently exploited for synthetic purposes. In this work, we identified potential halogenase sequences by screening algal, fungal, and protobacterial sequence databases, structural modeling of putative halogenases, and mapping and comparing active sites. In a final step, individual haloperoxidases were expressed and kinetically characterized. A vanadate-dependent haloperoxidase from Rhodoplanes roseus was heterologously expressible by E. coli and could be purified to homogeneity. The kinetic data revealed a higher turnover number than the known VClPO-CI and no inhibitory effect from bromide, rendering this enzyme a promising biocatalyst. Other predicted haloperoxidases were not expressed successfully yet but these enzymes were predicted to be present in a wide taxonomic variety.

Identification and Characterization of the Haloperoxidase VPO-RR from Rhodoplanes roseus by Genome Mining and Structure-Based Catalytic Site Mapping https://www.mdpi.com/1873100 #mdpicatalysts via @Catalysts_MDPI

Check it out :)

Check out our article on @ChemCatChem Covalently Immobilized 2‐Deoxyribose‐5‐phosphate Aldolase (DERA) for Biocatalysis in Flow: Utilization of the 3‐Hydroxyaldehyde Intermediate in Reaction Cascades https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.202200390#.YoOSzc-RwqY.twitter

Recent Advances in Biocatalysis for Drug Synthesis Biocatalysis is constantly providing novel options for the synthesis of active pharmaceutical ingredients (APIs). In addition to drug development and manufacturing, biocatalysis also plays a role in drug discovery and can support many active ingredient syntheses at an early stage to build up entire scaffolds in a targeted and preparative manner. Recent progress in recruiting new enzymes by genome mining and screening or adapting their substrate, as well as product scope, by protein engineering has made biocatalysts a competitive tool applied in academic and industrial spheres. This is especially true for the advances in the field of nonribosomal peptide synthesis and enzyme cascades that are expanding the capabilities for the discovery and synthesis of new bioactive compounds via biotransformation. Here we highlight some of the most recent developments to add to the portfolio of biocatalysis with special relevance for the synthesis and late-stage functionalization of APIs, in order to bypass pure chemical processes.

Recent Advances in Biocatalysis for Drug Synthesis https://www.mdpi.com/1598534 #mdpibiomedicines via @Biomed_MDPI

Glad to share this great Cooperation with colleagues from IMET : Catalytically Active Inclusion Bodies─Benchmarking and Application in Flow Chemistry https://pubs.acs.org/doi/10.1021/acssynbio.2c00035#.YoOQhj6qL30.twitter
@krauss_ulrich
@ACSPublications

Check out our recent publication in Biotechnology Progress about a non-invasive method for optimizing the cultivation conditions of Pseudomonas putida KT2440 for the production of the natural product #prodigiosin.

https://aiche.onlinelibrary.wiley.com/doi/full/10.1002/btpr.3245

Promotion im IBOC Wir besetzen aktuell vier Doktorandenstellen in der (Bio)katalyse in der Durchfluss-Chemie (Flow-Chemie), der Natur- und Wirkstoffsynthese, Synthetische Enzymologie und Alkaloid-Semisynthese. Weitere Informationen gibt unter Stellenausschreibungen.

Currently we are looking for four motivated PhD students for exciting projects. Do not hesitate to apply.

https://www.iboc.uni-duesseldorf.de/aktivitaeten/aktuelles-/-termine/aktuelles-detail/ausschreibung-fuer-vier-doktorarbeiten

Herzlichen Glückwunsch an unseren lieben Kollegen Tom. Wir freuen uns unglaublich für dich! 🥳 https://x.com/SeLL_hhu/status/1463870102470856711

Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines 1,2,3,4-Tetrahydroisoquinolines form a valuable scaffold for a variety of bioactive secondary metabolites and commercial pharmaceuticals. Due to the harsh or complex conditions of the conventional chemical synthesis of this molecular motif, alternative mild reaction pathways are in demand. Here we present an easy-to-operate chemoenzymatic one-pot process for the synthesis of tetrahydroisoquinolines starting from benzylic alcohols and an amino alcohol. We initially demonstrate the oxidation of 12 benzylic alcohols by a laccase/TEMPO system to the corresponding aldehydes, which are subsequently integrated in a phosphate salt mediated Pictet–Spengler reaction with m-tyramine. The reaction conditions of both individual reactions were analyzed separately, adapted to each other, and a straightforward one-pot process was developed. This enables the production of 12 1,2,3,4-tetrahydroisoquinolines with yields of up to 87% with constant reaction conditions in phosphate buffer and common laboratory glass bottles without the supplementation of any additives.

Check out our new publication in @Catalysts_MDPI about the Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
#hhu_de
#hhu_iboc

https://www.mdpi.com/2073-4344/11/11/1389

Herzlichen Glückwunsch Kooperationen bringen oft erfolgreiche Publikationen mit sich, so auch wieder die Zusammenarbeit mit unserem Nachbarinstitut IMET. Fabian Hogenkamp und Fabienne Hilgers aus dem IMET, gelang es, gemeinsam mit Kollegen aus beiden Instituten neue optochemische Werkzeuge für die Expressionskontrolle in E. coli zu synthetisieren, zu charakterisieren und anzuwenden. Die Ergebnisse wurden nun in ChemBioChem veröffentlicht. Wir freuen uns und gratulieren allen Beteiligten ganz herzlich.

There is a new article we have published in @ChemBioChem with the title Optochemical control of bacterial gene expression - novel
photocaged compounds for different promoter systems.

https://t.co/B3Qai4uNuw

#HHU_de
#HHU_IBOC

We are proud to share the recent publication of Patrick Ullrich. He reported about the allylation of N-unsubstituted Imins in a one-pot approach.
#HHU_de
#HHU_IBOC

https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202101078

Herzlichen Dank! In den zurückliegenden zwei Jahren wurden etliche Lehrveranstaltungen kurzfristig auf Onlinemodule umgestellt. Dieses Format war für uns alle neu aber mit viel Einsatz war es uns doch möglich, unseren Studierenden spannende Module anzubieten. Die Lehrpreisnominierung 2021 für Thomas Classen (Chemie für Mediziner) und Jörg Pietruszka (Enzymtechnologie I) freut uns umso mehr und macht uns unglaublich stolz. Wir möchten hiermit allen Mitwirkenden und natürlich den Studierenden ganz herzlich danken! Ohne Euren Einsatz und Eure Flexibilität wären die letzten zwei Jahre so nicht möglich gewesen.

We are very excited to announce that two of our courses have been nominated for the 2020 Teaching Award. We are very grateful and proud.
#hhu_de
#hhu_iboc

https://www.iboc.uni-duesseldorf.de/aktivitaeten/aktuelles-/-termine/aktuelles-detail/lehrpreisnominierung-2020

Werkzeuge, Wirkstoffe & Wissenschaft Weitere Informationen zu unseren Aktivitäten in Forschung und Lehre finden Sie auf unserer Homepage unter https://www.iboc.hhu.de/. Wir freuen uns über Ihr Interesse zu Abschlussarbeiten, Modulen, Praktika oder Dissertationen. Kontaktieren Sie uns gerne über Sonja Meyer zu Berstenhorst via lehre-iboc@hhu.de - dann findet Ihre Mail den richtigen Weg, egal ob Sie sich für das Institut für Bioorganische Chemie oder auch für die Nachwuchsgruppe Sekundärmetabolismus-Enzymologie interessieren.

In this short image video we share insights from our institut.
#hhu_iboc
#hhu_de
#fzjuelich

https://mediathek.hhu.de/watch/399f46c1-286d-4c10-b3fe-2d450a08fc0d

We are excited to announce another publication in the @angew_chem. Pascal Schneider shares his fascinating results on the biocatalytic C3-indole methylation for stereoselective synthesis of pyrroloindoles. Congratulations Pascal!
#HHU_IBOC

https://onlinelibrary.wiley.com/doi/10.1002/anie.202107619

Great publication in Org. Lett. @JOC_OL from Pascal Schneider in cooperation with Department of Biochemical and Chemical Engineering & Department of Chemistry and Chemical Biology @TU_Dortmund, @SwissTPH, @UniBasel and IBG-1 Biotechnologie, @fz_juelich

https://t.co/mGwoLGVpwv

A few days ago, another contribution made by us was published on the IBG Bioeconomy Blog. #hhu_iboc
#hhu_de
#fzjuelich https://blogs.fz-juelich.de/biooekonomie/2021/06/28/hindenburg-h-milch-und-enzyme-wie-im-fluss-alles-einfacher-wird/

Nikolai Huwa, as first author, was able to conduct his first studies on OsJAC1, a protein from rice that confers resistance to powdery mildew, among other things.
Congratulations!
#HHU_IBOC #HHU_de

https://t.co/Ck9nADGYKh