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Inspired by biological structural dynamics, we construct two chiral copper-based hydrogen-bonded frameworks [<jats:italic>D<\/jats:italic>(<jats:italic>L<\/jats:italic>)-Cu-crystals] via hydrogen-bonded assembly using chiral metal-organic helical as the building unit. Single-crystal X-ray diffraction elucidates hierarchical chirality evolution from asymmetric coordinations to helical chains and framework packing. Furthermore, disassembling <jats:italic>D<\/jats:italic>(<jats:italic>L<\/jats:italic>)-Cu-crystals yields corresponding single-unit chiral metal-organic helices [<jats:italic>D<\/jats:italic>(<jats:italic>L<\/jats:italic>)-Cu-SMOHs], fully exposed active sites and well-preserved helical architectures. Notably, <jats:italic>D<\/jats:italic>(<jats:italic>L<\/jats:italic>)-Cu-SMOHs inhibit amyloid fibrillization effectively with pronounced chirality discrimination, driven by entropy-favored hydrophobic interaction. Molecular docking reveals that <jats:italic>D<\/jats:italic>-Cu-SMOH exhibits enhanced binding to critical amyloidogenic regions relative to the <jats:italic>L<\/jats:italic>-enantiomer. This work establishes a dynamic and reversible assembly-disassembly approach applicable for constructions of chiral nanomaterials. 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