 Shiral hydrogen-bond organic inorganic frameworks, HOIFs, are synthesized via biomimicking self-assembly from amino acids to proteins, exhibiting remarkable chiroctical activity including untouched shiral fluorescence and enantiodeiscrimination of shiral aliphatic substrates. The disassembled HOIFs can be facially regenerated and self-purified via a protic solvent-induced reassembly, leading to at least three consecutive cycles without losing in antioselectivity. The underlying mechanism of chirality bias is decoded by experimental isothermal titration calorimetry and theoretical simulation. This article was authored by Zhang Wei, Yulong Duan, Yunling Geo, and others.