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Water‐soluble chiral metallopeptoids
Author(s) -
Baskin Maria,
Maayan Galia
Publication year - 2015
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.22675
Subject(s) - chemistry , circular dichroism , peptoid , metal ions in aqueous solution , chirality (physics) , intramolecular force , combinatorial chemistry , metal , titration , peptidomimetic , folding (dsp implementation) , chelation , stereochemistry , peptide , organic chemistry , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , electrical engineering , engineering , quantum mechanics , quark
Metal ions play a significant role in the activity of biological systems including catalysis, recognition and folding. Therefore, introducing metal ions into peptidomimetic oligomers is a potential way for creating biomimetic metal complexes toward applications in sensing, recognition, drug design and catalysis. Herein we report the design, synthesis and characterization of water‐soluble chiral N‐substituted glycine oligomers, “peptoids,” with one and two distinct intramolecular binding sites for metal ions such as copper and cobalt. We demonstrate for the first time the incorporation of the chiral hydrophilic group (S)‐(+)‐1‐methoxy‐2‐propylamine (Nsmp) within peptoid sequences, which provides both chirality and water solubility. Two peptoids, a heptamer, and a dodecamer bearing two and four 8‐hydroxyquinoline (HQ) groups respectively as metal‐binding ligands, were synthesized on solid support using the submonomer approach. Using UV‐titrations and ESI‐MS analysis we demonstrate the creation of a novel metallopeptoid bearing two metal ions in distinct binding sites via intramolecular chelation. Exciton couplet circular dichroism (ECCD) demonstrated chiral induction from the chiral non‐helical peptoids to the metal centers. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 577–584, 2015.