Foldamers are oligomers that have secondary structures stabilized by noncovalent interactions which could be designed to potentially assume important biochemical functions. This project involves the synthesis of monomer units of foldamers. Our goals are to synthesize the monomers, determine their preferred conformations using NOE NMR experiments, and compare the conformational data derived from NMR experiments to conformational data obtained for the same molecules by the Pophristic's group using computational methods.  Here we describe our initial synthetic efforts, and preliminary NMR data.The target molecules N,N-dimethyl-2,6-pyridinedicarboxamide(A) and 3-acetylamino-N-methylbenzamide(B) were synthesized in 53 and 21 % overall yield respectively from readily available materials. The conformational preferences of 3-acetylamino-N-methylbenzamide were studied by NOE NMR in deuterated DMSO and water, in deuterated methanol, and in deuterated chloroform.

Synthesis and NMR characterization of monomer units of foldamers

248th National Meeting (2014)

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