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Sequence‐Selective Recognition of Peptides in Aqueous Solution: A Supramolecular Approach through Micellar Imprinting
Author(s) -
Zhao Yan
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801401
Subject(s) - supramolecular chemistry , peptide , combinatorial chemistry , molecular recognition , molecular imprinting , micelle , chemistry , hydrogen bond , hydrophobic effect , sequence (biology) , imprinting (psychology) , aqueous solution , molecular binding , binding selectivity , selectivity , molecule , organic chemistry , biochemistry , catalysis , gene
Sequence‐selective recognition of peptides in water has been one of the most important and yet unsolved problems in bioorganic and supramolecular chemistry. The motivation comes from not only the importance of these molecules in biology but also the fundamental challenges involved in the research. Molecular imprinting in doubly cross‐linked surfactant micelles offers a unique solution to this problem by creating a “supramolecular code” on the micelle surface that matches the structural features of the peptide chain. Hydrophobic “dimples” are constructed on imprinted micelles that match the hydrophobic side chains of the peptide precisely in size and shape. Polar binding functionalities are installed at correct positions to interact with specific acidic and basic groups on the peptide. Secondary hydrogen‐bonding and electrostatic interactions are introduced through imprinting to enhance the binding affinity and specificity further. Binding affinities of tens of nanomolar are readily achieved in water for biological peptides with over a dozen residues. Excellent binding selectivity is observed even for subtly different peptides. The synthesis of these protein‐sized nanoparticles involves a one‐pot reaction complete within 2 days; purification requires nothing but precipitation and solvent washing. These features make the molecularly imprinted nanoparticles (MINPs) highly promising peptide‐binding “artificial antibodies” for chemical and biological applications.