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Aromatic oligoesters as novel helix mimetic scaffolds.

ABSTRACT: The design, synthesis, and conformational analysis of a novel aromatic oligoester helix mimetic scaffold is reported. A range of amino acid-type side-chain functionality can be readily incorporated into monomer building blocks over three facile synthetic steps. Analysis of representative dimers revealed a stable conformer capable of effective mimicry of a canonical α-helix and the scaffold was found to be surprisingly stable to degradation in aqueous solutions at acidic and neutral pH.

SUBMITTER: Haque M

PROVIDER: S-EPMC10250785 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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Aromatic oligoesters as novel helix mimetic scaffolds.

Haque Muhammed M Flack Theo T Singh Ravi R Wall Archie A de Castro Guilherme Vieira GV Jiang Lishen L White Andrew J P AJP Barnard Anna A

Bioorganic & medicinal chemistry 20230507

The design, synthesis, and conformational analysis of a novel aromatic oligoester helix mimetic scaffold is reported. A range of amino acid-type side-chain functionality can be readily incorporated into monomer building blocks over three facile synthetic steps. Analysis of representative dimers revealed a stable conformer capable of effective mimicry of a canonical α-helix and the scaffold was found to be surprisingly stable to degradation in aqueous solutions at acidic and neutral pH. ...[more]

PMID: 37182518

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