Bis-peptides are rigid, oligomeric structures formed from 4-hydroxyproline derived building blocks.  These bis-amino acid building blocks are connected through pairs of amide bonds to form diketopiperazine (DKP) linkages.  Bis-peptides bearing functionality at the nitrogen of the DKP have been previously synthesized to create alpha-helical presentations of functional groups for peptidomimetics.  As an extension of this, bis-amino acids have been alkylated at the alpha (C-2) position.  It has been found that under strong basic conditions, bis-amino acids are alkylated with a variety of benzylic and allylic halides.  By incorporating this methodology along with the N-alkylation strategy, oligomers can be assembled that carry many functional groups with different orientations in a compact space.  These highly functionalized bis-peptides will be designed and implemented as small molecule targets for binding protein surfaces.

Increasing the degree of functionalization of <i>bis</i>-peptide oligomers through a C-alkylation strategy

244th National Meeting (2012)

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Increasing the degree of functionalization of bis-peptide oligomers through a C-alkylation strategy