Traditional natural product isolation is an extensive and laborious process that can require several rounds of purification, provide low compound yields, or re-discovery of known molecules.  Natural products represent approximately 40% of today's therapeutic agents and continually play an important role in drug discovery.  A major bottleneck in the discovery process lies in the separation techniques, which disperse molecules by size, polarity, or charge; therefore, new methods should increase the relative concentration of potentially active compounds and reduce interference from other components in the initial mixture.  We have generated a novel method for the separation of molecules by functional group-mediated isolation.  This enrichment technique utilizes a reactive group affixed to a solid-phase resin to immobilize compounds, enabling their chemoselective enrichment, followed by the release of the unaltered chemical structures.  To date, two enrichment tags have been developed to target molecules that contain the hydroxyl or carboxylic acid functional group.  Because 65% of natural products contain the hydroxyl functional group, it would be beneficial to further divide this group into sub groups, i.e. primary, secondary, tertiary alcohols, phenols, and diols.  Here, we developed a new enrichment tag that enables parsing of 1,2- or 1,3-diol-containing compounds.

Chemoselective enrichment of 1,2- or 1,3-diol-containing compounds for natural product isolation

246th National Meeting (2013)

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