We report the fluorenylmethoxycarbonyl
(Fmoc) protection of functionalized
bis-amino acid building blocks using a temporary Cu2+ complexation
strategy, together with an efficient multikilogram-scale synthesis
of bis-amino acid precursors. This allows the synthesis of stereochemically
and functionally diverse spiroligomers utilizing solid-phase Fmoc/tBu
chemistry to facilitate the development of applications. Four tetramers
were assembled on a semiautomated microwave peptide synthesizer. We
determined their secondary structures with two-dimensional nuclear
magnetic resonance spectroscopy.
Here, we report a new class of peptidomimetic macrocycles with well-defined three-dimensional structures and low conformational flexibility. They are assembled from fused-ring spiro-ladder oligomers (spiroligomers) by modular solid-phase synthesis. Twodimensional nuclear magnetic resonance confirms their shape persistency. Triangular macrocycles of tunable sizes assemble into membranes with atomically precise pores, which exhibit size and shape-dependent molecular sieving towards a series of structurally similar compounds. The exceptional structural diversity and stability of spiroligomer-based macrocycles will be explored for more applications.
Here, we report a new class of peptidomimetic macrocycles with well-defined three-dimensional structures and low conformational flexibility. They are assembled from fused-ring spiro-ladder oligomers (spiroligomers) by modular solid-phase synthesis. Twodimensional nuclear magnetic resonance confirms their shape persistency. Triangular macrocycles of tunable sizes assemble into membranes with atomically precise pores, which exhibit size and shape-dependent molecular sieving towards a series of structurally similar compounds. The exceptional structural diversity and stability of spiroligomer-based macrocycles will be explored for more applications.
Metrics & MoreArticle Recommendations * sı Supporting Information H ere we provide 2D NMR spectra and assignments of T1−T4, which are missing from the Supporting Information in the original version of publication.
■ ASSOCIATED CONTENT
* sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c00270.2D NMR spectra and assignments of T1−T4 (PDF)
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