Organic and bioorganic synthesis
Prof. dr. J. Van der Eycken

Postdoctoral researchers
   
PhD students
Frederique Backaert  
Katrien Bert  
Simon Cogen  
Jelle Cornelus  
Ine De Vilder  
Yasar Gök  
Pieter Janssens  
Timothy Noël  
Sam Pieters  

Punit Kumar Rasadia

  
Rosa Romeralo Tapia  
Karel-Simon Slock  
   
Other staff
Frank Becu  
Jurgen Caroen  
Jan Goeman  

Research topics

  • Synthesis of compounds with biological activity, e.g. the antitumor compound podophyllotoxin and its analogues, carba- or pseudo-sugars as glycosidase inhibitors with potential antiviral and anti-AIDS activity, inositol analogues as secondary cellular messengers.

  • Synthesis of novel fluorizers for detection of gene expression.

  • Development of new homochiral building blocks using enzymatic catalysis: lipase-catalyzed enantio(topo)differentiation of cyclic and acyclic polyol derivatives.

  • Synthesis of new homochiral ligands for asymmetric transition metal catalysis.

  • Asymmetric synthesis based upon transition metal catalysis.

  • Combinatorial libraries: design and synthesis of new types of combinatorial libraries, which will be screened for biological activity. Emphasis will be on the construction of carbohydrate-based libraries, and on peptide or peptoid libraries with enzymatic activity.

Perspectives:

  • Research on combinatorial libraries will be one of our priorities. With this approach, new lead structures with interesting biological activities can be discovered quickly from a large pool of compounds. Industrial partners and university laboratories with complementary know-how are welcome to collaborate.

  • The synthesis of novel fluorisers will allow determination of foreign gene expression in plants with high sensitivity and resolution. This is done by confocal microscopy in collaboration with the Department of Molecular Genetics (Prof. M. Van Montagu) and the VIB (Flemish Interuniversity Institute for Biotechnology).

  • Synthesis of natural products with biological activity, and synthesis of designed analogues with tailored properties will be an important part of our investigation. For this topic, collaboration with interested industrial partners will be sought.

  • Development of new catalysts for asymmetric synthesis is also a reseach topic with high priority. The use of enzymes, other than lipases, in organic synthesis, as well as the design and synthesis of new homochiral ligands for transition metal catalysis will be investigated.

 

Publications

2009

Caroen, Jurgen; Van der Eycken, Johan. A sensitive and practical colorimetric test for polymer-supported hydroxyl and thiol groups. Tetrahedron Letters (2009), 50(1), 41-44.

2008

Espeel, Pieter E. R.; Piens, Kathleen; Callewaert, Nico; Van der Eycken, Johan. Synthesis of isofagomine and a new C6 pyrrolidine azasugar with potential biological activity. Synlett (2008), (15), 2321-2325.

2007

Noel, Timothy; Vandyck, Koen; Van der Eycken, Johan. Some new C2-symmetric bicyclo[2.2.1]heptadiene ligands: synthesis and catalytic activity in rhodium(I)-catalyzed asymmetric 1,4- and 1,2-additions. Tetrahedron (2007), 63(52), 12961-12967.

Devreux, Vincent; Wiesner, Jochen; Jomaa, Hassan; Van der Eycken, Johan; Van Calenbergh, Serge. Synthesis and evaluation of a , b -unsaturated a -aryl-substituted fosmidomycin analogues as DXR inhibitors. Bioorganic & Medicinal Chemistry Letters (2007), 17(17), 4920-4923.

Ruttens, Bart; Blom, Petra; Van Hoof, Steven; Hubrecht, Idzi; Van der Eycken, Johan; Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan. Carbohydrate-Based Macrolides Prepared via a Convergent Ring Closing Metathesis Approach: In Search for Novel Antibiotics. Journal of Organic Chemistry (2007), 72(15), 5514-5522.

Kuppens, Tom; Vandyck, Koen; Van der Eycken, Johan; Herrebout, Wouter; Van der Veken, Benjamin; Bultinck, Patrick. A DFT conformational analysis and VCD study on methyl tetrahydrofuran-2-carboxylate. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2007), 67A(2), 402-411.

Devreux, Vincent; Wiesner, Jochen; Jomaa, Hassan; Rozenski, Jef; Van der Eycken, Johan; Van Calenbergh, Serge. Divergent Strategy for the Synthesis of a -Aryl-Substituted Fosmidomycin Analogues. Journal of Organic Chemistry (2007), 72(10), 3783-3789.

Kaval, Nadya; Singh, Brajendra Kumar; Ermolat'ev, Denis S.; Claerhout, Stijn; Parmar, Virinder S.; Van der Eycken, Johan; Van der Eycken, Erik. Transition Metal-Catalyzed Orthogonal Solid-Phase Decoration of the 2(1H)-Pyrazinone Scaffold Using a Sulfur Linker. Journal of Combinatorial Chemistry (2007), 9(3), 446-453.

Schepers, Eva; Meert, Natalie; Glorieux, Griet; Goeman, Jan; Van der Eycken, Johan; Vanholder, Raymond. P-cresylsulphate, the main in vivo metabolite of p-cresol, activates leucocyte free radical production. Nephrology, Dialysis, Transplantation (2007), 22(2), 592-596.

Debie, Elke; Kuppens, Tom; Vandyck, Koen; Van der Eycken, Johan; Van Der Veken, Benjamin; Herrebout, Wouter; Bultinck, Patrick. Vibrational circular dichroism DFT study on bicyclo[3.3.0]octane derivatives. Tetrahedron: Asymmetry (2007), Volume Date 2006, 17(23), 3203-3218.

2006

Devreux, Vincent; Wiesner, Jochen; Goeman, Jan L.; Van der Eycken, Johan; Jomaa, Hassan; Van Calenbergh, Serge. Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors. Journal of Medicinal Chemistry (2006), 49(8), 2656-2660.

Van Hoof, Steven; Ruttens, Bart; Hubrecht, Idzi; Smans, Gert; Blom, Petra; Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan; Van der Eycken, Johan. Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals. Bioorganic & Medicinal Chemistry Letters (2006), 16(6), 1495-1498.

Van der Eycken, Johan. Preparation of monosaccharides and disaccharides simmondsin analogs as antitumor agents and angiogenesis inhibitors in study of drug discovery. Eur. Pat. Appl. (2006), 27 pp.

Vandyck, Koen; Matthys, Bavo; Willen, Mario; Robeyns, Koen; Van Meervelt, Luc; Van der Eycken, Johan. Rhodium-Catalyzed Asymmetric Conjugate Additions of Boronic Acids to Enones Using DIPHONANE: A Novel Chiral Bisphosphine Ligand. Organic Letters (2006), 8(3), 363-366.

2005

Blom, Petra; Ruttens, Bart; Van Hoof, Steven; Hubrecht, Idzi; Van der Eycken, Johan; Sas, Benedikt; Van hemel, Johan; Vandenkerckhove, Jan. A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity. Journal of Organic Chemistry (2005), 70(24), 10109-10112.

Kuppens, T.; Vandyck, K.; Van der Eycken, J.; Herrebout, W.; van der Veken, B. J.; Bultinck, P. Determination of the Absolute Configuration of Three as-Hydrindacene Compounds by Vibrational Circular Dichroism. Journal of Organic Chemistry (2005), 70(23), 9103-9114.

Kaval, Nadya; Halasz-Dajka, Beata; Vo-Thanh, Giang; Dehaen, Wim; Van der Eycken, Johan; Matyus, Peter; Loupy, Andre; Van der Eycken, Erik. An efficient microwave-assisted solvent-free synthesis of pyrido-fused ring systems applying the tert-amino effect. Tetrahedron (2005), 61(38), 9052-9057.

Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan; Peys, Eric; Van Der Eycken, Johan; Ruttens, Bart; Blom, Petra. Bicyclic carbohydrate compounds useful in the treatment of infections caused by Herpesviridae. U.S. Pat. Appl. Publ. (2005), 18 pp.

Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan; Peys, Eric; Van Der Eycken, Johan; Van Hoof, Steven. Preparation of bicyclic glycosides as antiviral agents for the treatment of infections caused by the Alphaherpesvirinae HSV-1 and HSV-2. U.S. Pat. Appl. Publ. (2005), 15 pp.

Mangelinckx, Sven; Boeykens, Marc; Vliegen, Maarten; Van der Eycken, Johan; De Kimpe, Norbert. Synthesis of new 3,3-dimethoxyazetidine-2-carboxylic acid derivatives. Tetrahedron Letters (2005), 46(3), 525-529.

2004

Van der Eycken, Erik; Van der Eycken, Johan; Editors. Microwaves in combinatorial and high-throughput synthesis. [In: QSAR Comb. Sci.; 2004, 23(10)]. (2004), 161 pp.

Van der Eycken, Erik; Van der Eycken, Johan. Editorial: Microwaves in combinatorial and high-throughput synthesis. QSAR & Combinatorial Science (2004), 23(10), 825.

Morreel, Kris; Ralph, John; Lu, Fachuang; Goeminne, Geert; Busson, Roger; Herdewijn, Piet; Goeman, Jan L.; Van der Eycken, Johan; Boerjan, Wout; Messens, Eric. Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols. Plant Physiology (2004), 136(4), 4023-4036.

Vandyck, Koen; Matthys, Bavo; Van der Eycken, Johan. Synthesis and absolute configuration of (1S,8S)-as-hydrindacene-1,8-diol as determined by the circular dichroism exciton chirality method. Tetrahedron Letters (2004), Volume Date 2005, 46(1), 75-78.

Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan; Peys, Eric; Van Der Eycken, Johan; Van Hoof, Steven. Antiviral furanose-type bicyclic carbohydrates. PCT Int. Appl. (2004), 28 pp.

Appukkuttan, Prasad; Orts, Amparo Baiget; Chandran, R. Prakash; Goeman, Jan. L.; Van der Eycken, Johan; Dehaen, Wim; Van der Eycken, Erik. Generation of a small library of highly electron-rich 2-(hetero)aryl-substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue. European Journal of Organic Chemistry (2004), (15), 3277-3285.

Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan; Van Hemel, Johan; Peys, Eric; Van Der Eycken, Johan; Ruttens, Bart; Van Hoof, Steven. Bicyclic carbohydrates as antiprotozoal bioactive for the treatment of infections caused by parasites. PCT Int. Appl. (2004), 26 pp.

Sas, Benedikt; Van Hemel, Johan; Vandenkerckhove, Jan; Peys, Eric; Van Der Eycken, Johan; Ruttens, Bart; Balzarini, Jan; Declercq, Erik; Nuyts, Johan. Bicyclic carbohydrate compounds useful in the treatment of infections caused by Flaviviridae sp., such as hepatitis C and bovine viral diarrhea viruses. PCT Int. Appl. (2004), 23 pp.

Goeman, Jan Ludwig; Van Acker, Koenraad Lodewijk August; Van Der Eycken, Johan Theo Andre; Dierynck, Inge. Membrane-permeable fluorogenic enzyme substrates and methods of preparation. PCT Int. Appl. (2004), 53 pp.

Gedey, S.; Van der Eycken, J.; Fueloep, F. Synthesis of alicyclic b -lactams via the Ugi reaction on a solid support. Letters in Organic Chemistry (2004), 1(3), 215-220.

Maubach, Julie; Depypere, Herman T.; Goeman, Jan; van der Eycken, Johan; Heyerick, Arne; Bracke, Marc E.; Blondeel, Philippe; de Keukeleire, Denis. Distribution of soy-derived phytoestrogens in human breast tissue and biological fluids. Obstetrics & Gynecology (Hagerstown, MD, United States) (2004), 103(5, Pt. 1), 892-898.

2003

Kaval, Nadya; Van Der Eycken, Johan; Caroen, Juergen; Dehaen, Wim; Strohmeier, Gernot A.; Kappe, C. Oliver; Van Der Eycken, Erik. An Exploratory Study on Microwave-Assisted Solid-Phase Diels-Alder Reactions of 2(1H)-Pyrazinones: the Elaboration of a New Tailor-Made Acid-Labile Linker. Journal of Combinatorial Chemistry (2003), 5(5), 560-568.

Sas, Benedikt; Van Der Eycken, Johan; Van Hemel, Johan; Blom, Petra; Vandenkerckhove, Jan; Ruttens, Bart. Preparation and use of glycoside-based ring structures with antimicrobial and cytostatic activity. PCT Int. Appl. (2003), 99 pp.

2002

Van der Eycken, Johan. The Nobel Prize for Chemistry for 2001. Chemie Magazine (Heverlee, Belgium) (2002), (1), 22-28.

De Coster, Gert; Vandyck, Koen; Van der Eycken, Erik; Van der Eycken, Johan; Elseviers, Myriam; Roper, Harald. D-Isomannide in synthesis: asymmetric Diels-Alder reactions with novel homochiral bis-imine Cu2+-catalysts. Tetrahedron: Asymmetry (2002), 13(15), 1673-1679.

Gedey, Szilvia; Van der Eycken, Johan; Fülop, Ferenc. Liquid-Phase Combinatorial Synthesis of Alicyclic b -Lactams via Ugi Four-Component Reaction. Organic Letters (2002), 4(11), 1967-1969.

Ruttens, Bart; Van der Eycken, Johan. Solid-phase synthesis of a new class of oligosaccharide analogues based on azasugars. Tetrahedron Letters (2002), 43(12), 2215-2221.

2001

Courtyn, Jan; Goethals, Patrick; Van der Eycken, Johan; Dams, Richard. Synthesis of 11C-labelled acamprosate for PET studies. Journal of Labelled Compounds & Radiopharmaceuticals (2001), 44(9), 643-651.

Peter, A.; Kaman, J.; Fulop, F.; van der Eycken, J.; Armstrong, D. W. High-performance liquid chromatographic enantioseparation of bicyclic 1,3-amino alcohols. Journal of Chromatography, A (2001), 919(1), 79-86.

Steelant, Wim F. A.; Goeman, Jan L.; Philippe, Jan; Oomen, Lauran C. J. M.; Hilkens, John; Krzewinski-Recchi, Marie-Ange; Huet, Guillemette; Van der Eycken, Johan; Delannoy, Philippe; Bruyneel, Erik A.; Mareel, Marc M. Alkyl-lysophospholipid 1-o-octadecyl-2-o-methyl-glycerophosphocholine induces invasion through episialin-mediated neutralization of E-cadherin in human mammary MCF-7 cells in vitro. International Journal of Cancer (2001), 92(4), 527-536.

Kaman, J.; Van der Eycken, J.; Peter, A.; Fulop, F. Enzymatic resolution of bicyclic 1,3-amino alcohols in organic media. Tetrahedron: Asymmetry (2001), 12(4), 625-631.

Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron (2001), 57(14), 2781-2786.

2000

Salgado, Antonio; Eeckhaut, Annelies; De Kimpe, Norbert; Van der Eycken, Johan. Enzyme-mediated synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid. Proceedings of ECSOC-3, [and] Proceedings of ECSOC-4, Sept. 1-30, 1999 and 2000 (2000), Meeting Date 1999-2000, 629-635.

Van der Eycken, E.; Terryn, N.; Goeman, J. L.; Carlens, G.; Nerinckx, W.; Claeyssens, M.; Van der Eycken, J.; Van Montagu, M.; Brito-Arias, M.; Engler, G. Sudan- b -D-glucuronides and their use for the histochemical localization of b -glucuronidase activity in transgenic plants. Plant Cell Reports (2000), 19(10), 966-970.

Hubrecht, Idzi; Van der Eycken, Erik; Van der Eycken, Johan. Synthesis of 6a-carba- a - and 6a-carba- b -D-fructopyranose from an enzymatically resolved cyclohexanetriol building block. Synlett (2000), (7), 971-974.

Samyn, Bart; Hardeman, Klaas; Van der Eycken, Johan; Van Beeumen, Jozef. Applicability of the Alkylation Chemistry for Chemical C-Terminal Protein Sequence Analysis. Analytical Chemistry (2000), 72(7), 1389-1399.

1999

Peter, Maria; Bernath, Gabor; Fulop, Ferenc; Van Der Eycken, Johan. Chiral discrimination of cyclic 1,3-amino alcohol enantiomers. Magyar Kemiai Folyoirat (1999), 105(2), 61-70.

1998

Van der Eycken, J.; Vandewalle, M. Chemo-enzymic total synthesis of some conduritols, carbasugars and (+)-fortamine. Carbohydrate Mimics (1998), 209-221.

Peter, Maria; Peter, Antal; Van der Eycken, Johan; Csomos, Peter; Bernath, Gabor; Fulop, Ferenc. High-performance liquid chromatographic separation of enantiomers of cyclic 1,3-amino alcohol derivatives. Journal of Chromatography, A (1998), 816(2), 123-129.

Peter, Maria; Van Der Eycken, Johan; Bernath, Gabor; Fulop, Ferenc. Enzymic resolution of alicyclic 1,3-amino alcohols in organic media. Tetrahedron: Asymmetry (1998), 9(13), 2339-2347.

Hardeman, Klaas; Samyn, Bart; Van Der Eycken, Johan; Van Beeumen, Jozef. An improved chemical approach toward the C-terminal sequence analysis of proteins containing all natural amino acids. Protein Science (1998), 7(7), 1593-1602.

Van der Eycken, E.; Carlens, G.; Messens, J.; Zhao, Yining; Bauw, G.; Van der Eycken, J.; Sandra, P.; Van Montagu, M. Synthesis of l-xylo-hexos-2-ulose (l-sorbosone) and its characterization by chromatographic and spectroscopic techniques. Journal of Chromatography, A (1998), 811(1 + 2), 261-268.

De Smaele, Tom; Moens, Luc; Dams, Richard; Sandra, Pat; Van der Eycken, Johan; Vandyck, Jos. Sodium tetra(n-propyl)borate: a novel aqueous in situ derivatization reagent for the simultaneous determination of organomercury, -lead and -tin compounds with capillary gas chromatography-inductively coupled plasma mass spectrometry. Journal of Chromatography, A (1998), 793(1), 99-106.

1997

Goethals, Patrick; Volders, Filip; Van Der Eycken, Johan; Van Eijkeren, Marc; Lemahieu, Ignace; Dams, Richard. Synthesis of 6-methyl[11C]-2'-deoxyuridine and evaluation of its in vivo distribution in Wistar rats. Nuclear Medicine and Biology (1997), 24(8), 713-718.

Saeyens, Wim; Busson, Roger; Van der Eycken, Johan; Herdewijn, Piet; De Keukeleire, Denis. Fully selective intramolecular ortho photocycloaddition of 4-(4-methoxyphenoxy)-3-(N3-benzoylthymin-1-yl)but-1-ene: an unprecedented benzene-thymine photocycloaddition. Chemical Communications (Cambridge) (1997), (9), 817-818.

1996

Van der Eycken, Erik; De Keukeleire, Denis; Bruyn, Andre; Van der Eycken, Johan; Gilbert, Andrew. Stereochemical features of meta photocycloadducts derived from 3-alkyl-4-phenoxybut-1-enes. Recueil des Travaux Chimiques des Pays-Bas (1995), 114(11/12), 480-2.

 
PhD-Theses

  • Gert De Coster (1999) : "Valorisatie van 1,4:3,6-dianhydrohexitolen in asymmetrische synthese."

  • Jurgen Van Holen (2000) : "Synthese van harsgebonden combinatorische oligopeptedebibliotheken met potentiële glycosidase activiteit."

  • Idzi Hubrecht (2000) : "Valorisatie van carbocyclische en acyclische polyolderivaten in enantioselectieve synthese van pseudo-ketohexopyranosen, conduritolen en aminosuikers."

  • Klaas Hardeman (2000) : "..."

  • Bert Ruttens (2001) : "Ontwikkeling van een koppelingsstrategie voor de synthese van harsgebonden oligosacharide-analogen op basis van iminosuikers."

  • Petra Blom (2001) : "Synthese van van nieuwe macroliden met potentiële antibiotische activiteit uitgaande van suikers."

  • Dimitri De Conick (2003) : "Synthese van nieuwe liganden, afgeleid van suikers en enzymatisch geresolveerde bouwstenen voor toepassing in asymmetrische transitiemetaalkatalyse."

  • Maarten Vliegen (2005) : "Totaalsynthese van azetidine-analogen van castanospermine met potentiële biologische activiteit."

  • Elias Vervecken (2005) : "Ontwikkeling van nieuwe homochirale liganden voor asymmetrische transitiemetaal katalyse."

  • Tor Maes (2005) : "Cyclitolaminozuren : Synthese en valorisatie en de ontwikkeling van foldameren en analogen van glycogeconjugeerde peptiden."

  • Steven Van Hoof (2006) : "Synthese van nieuwe potente antivirale middelen gebaseerd op bicyclische C-glycosides."

  • Koen Vandyck (2006) : "Synthese en toepassing van rigide C2-symmetrische bidentaat liganden."

  • Vincent Devreux (2007) : "Synthese van fosmidomycine-analogen met potentiële antimalaria-activiteit."

  • Gert Smans (2008) : "Convergente en stereoselectieve synthese van het C1-C11 en het C12-C17 fragment van (+)-Peloruside A."

 
Equipment

  • Synthesis:

  • Separation and analysis :
    • 2 Varian model 3700 Gas Chromatographs for classic GC and chiral GC analysis.
    • Prep HPLC on a dual Kontron 422 HPLC pump system and a ternary Kontron 525 HPLC pump system with Melz lcd312 RI detector, Kontron 535 UV-VIS detector and Alltech 500 ELSD detector.
    • Agilent technologies 1100 series LC/MSD system (degasser / quaternary pump / autosampler / column oven with column changer / diode array detector / single quad MS detector (VL) with electrospray and APCI source) for classic reversed phase LCMS and chiral HPLC.
    • Varian Cary Eclipse Spectrofluorimeter
    • Hitachi U-2010 UV-VIS spectrophotometer
    • Perkin-Elmer Spectrum1000 FTIR infrared spectrometer with pike-HATR option.
    • Perkin-Elmer 2400 series II elemental analyzer.
    • Parr pressure reactor up to 4 bar : 100 mL - 2 L
    • High pressure reactors (Andreas-Hofer) up to 200 bar : 50 mL - 1 L

 

  • Computation & Simulation :
 

 

 

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