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Spatially Addressed Synthesis of Amino- and Amino-Oxy-Substituted 1,3,5-Triazine Arrays on Polymeric Membranes

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Institut für Medizinische Immunologie, Universitätsklinikum Charité, Humboldt-Universität zu Berlin, Schumannstr. 20-21, D-10098 Berlin, Germany, Jerini Bio Tools GmbH, Rudower Chaussee 29, D-12489 Berlin, Germany, and ChemotopiX GmbH, Rudower Chaussee 29, D-12489 Berlin, Germany
Cite this: J. Comb. Chem. 2000, 2, 4, 361–369
Publication Date (Web):May 26, 2000
https://doi.org/10.1021/cc000012g
Copyright © 2000 American Chemical Society
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    Abstract

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    Effective spatially addressed parallel assembly of trisamino- and amino-oxy-1,3,5-triazines was achieved by applying the SPOT-synthesis technique on cellulose and polypropylene membranes. In addition to developing a suitable linker strategy and employing amines and phenolate ions as building blocks, a highly effective microwave-assisted nucleophilic substitution procedure at membrane-bound monochlorotriazines was developed. The 1,3,5-triazines obtained could be cleaved in parallel from the solid support by TFA vapor to give compounds adsorbed on the membrane surface in a conserved spatially addressed format for analysis and screening. The reaction conditions developed were employed for the synthesis of 8000 cellulose-bound 1,3,5-triazines which were probed in parallel for binding to the anti-transforming growth factor-α monoclonal antibody Tab2 in order to identify epitope mimics.

    †

     Universitätsklinikum Charité.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    ‡

     Jerini Bio Tools GmbH.

    §

     ChemotopiX GmbH.

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    Purities of crude 1,3,5-triazines, obtained by selective “spot-wise” nucleophilic substitution of a single chlorine at cellulose or PP-membrane-bound dichlorotriazines, subsequent replacement of remaining chlorines by an appropriate amine,14 and cleavage by TFA. This material is available free of charge via the Internet at http://pubs.acs.org.

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