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Solid-Phase Synthesis and Circular Dichroism Study of ?-ABpeptoids.

ABSTRACT: The development of peptidomimetic foldamers that can form well-defined folded structures is highly desirable yet challenging. We previously reported on ?-ABpeptoids, oligomers of N-alkylated ?²-homoalanines and found that due to the presence of chiral methyl groups at ?-positions, ?-ABpeptoids were shown to adopt folding conformations. Here, we report ?-ABpeptoids having chiral methyl group at ?-positions rather than ?-positions as a different class of peptoids with backbone chirality. We developed a facile solid-phase synthetic route that enables the synthesis of ?-ABpeptoid oligomers ranging from 2-mer to 8-mer in excellent yields. These oligomers were shown to adopt ordered folding conformations based on circular dichroism (CD) and NMR studies. Overall, these results suggest that ?-ABpeptoids represent a novel class of peptidomimetic foldamers that will find a wide range of applications in biomedical and material sciences.

SUBMITTER: Sable GA 

PROVIDER: S-EPMC6337665 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Solid-Phase Synthesis and Circular Dichroism Study of β-ABpeptoids.

Sable Ganesh A GA   Lee Kang Ju KJ   Lim Hyun-Suk HS  

Molecules (Basel, Switzerland) 20190105 1

The development of peptidomimetic foldamers that can form well-defined folded structures is highly desirable yet challenging. We previously reported on α-ABpeptoids, oligomers of <i>N</i>-alkylated β²-homoalanines and found that due to the presence of chiral methyl groups at α-positions, α-ABpeptoids were shown to adopt folding conformations. Here, we report β-ABpeptoids having chiral methyl group at β-positions rather than α-positions as a different class of peptoids with backbone chirality. We  ...[more]

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