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Chemoselective Displacer Synthesis

Co-Investigator: James A. Moore

Professor, Department of Chemistry and Chemical Biology Rensselaer Polytechnic Institute
In ion exchange displacement chromatography high resolution separation of charged biomolecules (proteins, oligonucleotides) has been accomplished (Shukla et al., 2000; Tugcu et al., 2001; Tugcu et al., 2002; Tugcu et al., 2002; Rege et al., 2004). Ongoing efforts in this work are involved in designing displacer molecules that will demonstrate selectivity in the displacement of desired molecules. As shown below, a variety of different types of molecules are being prepared where structure is changed in a controlled manner to reveal the influence of properties such as polarity, charge, hydrophobicity and/or aromaticity on the efficacy of separations.

Using commercially available monoglycosides of glucose, galactose and mannose it is possible to vary the nature of the aglycone (R = methyl, octyl, phenyl, naphthyl). When sulfonated these frameworks will yield displacers with four sulfonate groups. It is also possible to partially protect two or four hydroxyl groups in trehalose by forming acetals with benzaldeyde thereby introducing aromatic character into a portion of these displacers that has not been functionalized in this way before. When sulfonated, these materials will bear four and six sulfate groups, respectively. Evaluation of the efficacy of these displacers in protein separation should grant insight into the way in which structure can be modulated to produce selective displacers.

The diversity-based synthesis and protein displacement efficacy assay components are part of an integrated displacer design strategy that includes the building of QSER models based on the behavior of existing compounds, and the synthesis and testing of new compounds suggested by modeling results.

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