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Related Concept Videos

Extraction: Advanced Methods00:56

Extraction: Advanced Methods

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Metal ions can be separated from one another by complexation with organic ligands–the chelating agent– to form uncharged chelates. Here, the chelating agent must contain hydrophobic groups and behave as a weak acid, losing a proton to bind with the metal. Since most organic ligands used in this process are insoluble or undergo oxidation in the aqueous phase, the chelating agent is initially added to the organic phase and extracted into the aqueous phase. The metal-ligand complex is...
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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Metal-Ligand Bonds02:51

Metal-Ligand Bonds

25.7K
The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
25.7K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.5K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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7.5K
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

4.1K
Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
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Related Experiment Video

Updated: Apr 12, 2026

Synthesis of a Water-soluble Metal&#8211;Organic Complex Array
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Synthesis of a Water-soluble Metal–Organic Complex Array

Published on: October 8, 2016

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Water-soluble chiral metallopeptoids.

Maria Baskin1, Galia Maayan1

  • 1Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 32000, Israel.

Biopolymers
|May 14, 2015
PubMed
Summary

Researchers created novel water-soluble peptoids with specific metal-binding sites. These biomimetic metal complexes show chiral induction, paving the way for new applications in sensing and catalysis.

Area of Science:

  • Biomimetic Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Metal ions are crucial for biological processes like catalysis and folding.
  • Incorporating metal ions into peptidomimetic oligomers offers a route to biomimetic complexes for various applications.
  • Peptoids (N-substituted glycine oligomers) are versatile scaffolds for designing functional molecules.

Purpose of the Study:

  • To design, synthesize, and characterize water-soluble chiral peptoids with distinct metal-binding sites.
  • To incorporate a chiral hydrophilic group (S)-(+)-1-methoxy-2-propylamine (Nsmp) for chirality and water solubility.
  • To create novel metallopeptoids capable of binding multiple metal ions in defined positions.

Main Methods:

  • Solid-phase synthesis of peptoid heptamer and dodecamer using the submonomer approach.
Keywords:
chiralitycoppermetallofoldamerpeptoid

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Structure and Coordination Determination of Peptide-metal Complexes Using 1D and 2D 1H NMR

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Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides
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Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides

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  • Incorporation of 8-hydroxyquinoline (HQ) groups as metal-binding ligands.
  • Characterization using UV-titrations, ESI-MS, and Exciton Couplet Circular Dichroism (ECCD).

    • Main Results:

    • Successful synthesis of water-soluble chiral peptoids with 8-hydroxyquinoline metal-binding sites.
    • Demonstration of metallopeptoid formation with two distinct metal-binding sites via intramolecular chelation.
    • Evidence of chiral induction from the peptoid backbone to the coordinated metal centers.

    Conclusions:

    • Novel water-soluble chiral peptoids with tunable metal-binding capabilities have been developed.
    • The synthesized metallopeptoids exhibit controlled metal coordination and chiral induction.
    • These findings open avenues for creating advanced biomimetic materials for sensing, catalysis, and drug design.