Synthesis of Stereodiverse Linear Compounds for Biological Evaluation

Mentors: Eamon Comer and Sarathy Kesavan

Diversity-oriented synthesis (DOS) is an effective method of chemical synthesis that allows the production of diverse collections of compounds. Joe and his mentors set out to prove the feasibility of using DOS to generate a new collection of molecules based on a linear core compound.   Joe synthesized one such linear core compound, which had two diversity sites to which he added a variety of chemical “building blocks.”  At each step, he used liquid chromatography/mass spectrometry to evaluate his success.  In this way, Joe generated six high purity compounds. 

Joe’s study has shown that the synthesis of a linear small molecule collection through DOS is feasible.  Based on his results, the full collection of 512 compounds will be produced.  Eight linear core compounds will be used, and eight building blocks will be added to each of two diversity sites on the core compounds.  This collection will then be tested for the ability of these compounds to modulate various biological processes.

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Joe, a senior at Cambridge Rindge and Latin School, synthesized a novel collection of chemical compounds based on a linear core structure.


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