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

Postdoctoral researchers
   
PhD students
An Clemmen  
Simon Cogen  
Jelle Cornelus  
Ine De Vilder  
Pieter Espeel  
Yasar Gök  
Timothy Noël  
Rosa Romeralo Tapia  
Karel-Simon Slock  
Michel Van Overschelde  
   
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

1992

  • X. Deruyttere, L. Dumortier, J. Van der Eycken and M. Vandewalle: "The total synthesis of (+)-Palitantin"; Synlett , 1992 , (1), 51-52.

  • L. Dumortier, P. Liu, S. Dobbelaere, J. Van der Eycken and M. Vandewalle: "Lipase-catalyzed enantiotoposelective hydrolysis of meso -compounds derived from 2-cyclohexene-1,4-diol: Synthesis of (-)-Conduritol C, (-)-Conduritol E, (-)-Conduritol F and a homochiral derivative of Conduritol A"; Synlett , 1992 , (3), 243-245.

  • L. Dumortier, J. Van der Eycken and M. Vandewalle: "Applications of enzymatically prepared homochiral cyclohexane building blocks: enantioselective synthesis of derivatives of unnatural shikimic acid and of pseudo-a-D-mannopyranose"; Synlett , 1992 , (3), 245-246.

1995

  • E. Van der Eycken, D. De Keukeleire, A. de Bruyn, J. Van der Eycken and A. Gilbert: "Stereochemical features of meta photocycloadducts derived from 3-alkyl-4-phenoxybut-1-enes."; Rec. Trav. Chim. Pays-Bas, 1995 , 114, 480-482.

1997

  • W. Saeyens, R. Busson, J. Van der Eycken, P. Herdewijn, D. De Keukeleire: "Fully selective intramolecular ortho photocycloaddition of 4-(4-methoxyphenoxy)-3-(N 3 -benzoylthymin-1-yl)-but-1-ene: an unprecedented benzene thymine photocycloaddition."; J. Chem. Soc., Chem. Commun., 1997 , (9), 817-818.

  • P. Goethals, F. Volders, J. Van der Eycken and R. Dams: "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.

1998

  • E. Van der Eycken, G. Carlens, J. Messens, Y. Zhao, G. Bauw, J. Van der Eycken, P. Sandra and M. Van Montagu: "Preparation, high-performance liquid and gas chromatographic analysis of L-xylo-hexos-2-ulose (L-sorbosone)."; J. Chromatogr. A, 1998 , 811, 261-268.

  • K. Hardeman, B. Samyn, J. Van der Eycken and J. Van Beeumen: "Progress towards chemical C-terminal sequence analysis of proteins containing all natural amino acids. Formation of proline thiohydantoin via the oxazolonium intermediate."; Protein Sci., 1998 , 7, 1593-1602.

  • M. Péter, A. Péter, J. Van der Eycken, P. Csomós, G. Bernáth and F. Fülöp: "HPLC separation of enantiomers of cyclic 1,3-amino alcohol derivatives." J. Chromatogr. A, 1998 , 816, 123-129.

  • M. Péter, J. Van der Eycken, G. Bernáth and F. Fülöp: "Enzymatic resolution of alicyclic 1,3-amino alcohols in organic media." Tetrahedron: Asymmetry, 1998 , 9, 2339-2347.

2000

  • B. Samyn, K. Hardeman, J. Van der Eycken and J. Van Beeumen: "Applicability of the alkylation chemistry for chemical C-terminal protein sequence analysis." Anal. Chem., 2000 , 72 (7), 1389-1399.

  • I. Hubrecht and J. Van der Eycken: "Total synthesis of pseudo-a- and pseudo-b-D-fructopyranose from an enzymatically resolved cyclohexanetriol building block." Tetrahedron: Asymmetry, 2000 , Synlett, (7), 971-974.

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

2001

  • A. Peter, J. Kaman, F. Fulop, J. Van der Eycken, D. W. Armstrong: "High-performance liquid chromatographic enantioseparation of bicyclic 1,3-amino alcohols."
    Journal of Chromatography A, 2001 , 919 , 79-86.

  • J. Kaman, J. Van der Eycken, A. Peter, F. Fulop: "Enzymatic resolution of bicyclic 1,3-amino alcohols in organic media."
    Tetrahedron Asymmetry 2001 , 12 , 625-631.
  • A. Salgado, T. Huybrechts, A. Eeckhaut, J. Van der Eycken, Z. Szakonyi Z, F. Fulop, A. Tkachev, N. De Kimpe: "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 , 2781-2786.
  • M. Peter, G. Bernath, F. Fulop, J. Van der Eycken: "Chiral discrimination of cyclic 1,3-amino alcohol enantiomers."
    Magyar Kemiai Folyoirat 1999 , 105 , 61-70.

2002

  • Ruttens B., Van der Eycken J.: "Solid-phase synthesis of a new class of oligosaccharide analogues based on azasugars." Tetrahedron Lett., 2002, 43 (12), 2215-2221.
  • Gedey S., Van der Eycken J., Fulop F.: "Liquid-phase combinatorial synthesis of alicyclic beta-lactams via Ugi four-component reaction." Org. Lett., 2002, 4 (11), 1967-1969.
  • De Coster G., Vandyck K., Van der Eycken E., Van der Eycken J., Elseviers M., Roper H.: "D-Isomannide in synthesis: asymmetric Diels-Alder reactions with novel homochiral bis-imine Cu2+-catalysts." Tetrahedron: Asymm., 2002, 13 (15), 1673-1679.
Theses

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

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

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

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

 
Equipment

 

Computation & Simulation :

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