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Related Concept Videos

Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

956
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
956
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

467
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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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

1.9K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
1.9K
Metal-Ligand Bonds02:51

Metal-Ligand Bonds

20.6K
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...
20.6K
Complexometric Titration: Ligands00:43

Complexometric Titration: Ligands

916
Different monodentate and polydentate ligands are used as complexing agents in complexometric titration reactions. The formation of complexes by mono- and bidentate ligands involves two or more intermediate steps, limiting their use as complexing agents. In comparison, polydentate ligands can form complexes with metal ions in a single-step process, facilitating sharper end points. This means polydentate ligands, such as amino carboxylic acid derivatives, are most commonly employed in...
916
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.2K

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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
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Heterotelechelic Organometallic PEG Reagents Enable Modular Access to Complex Bioconjugates.

Grace E Kunkel1, Joseph W Treacy1, Magdalena F Polite1

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.

ACS Macro Letters
|October 31, 2024
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Summary

Organometallic oxidative addition complexes (OACs) enable rapid, selective biomolecule modification. New gold(III) OACs facilitate regioselective S-arylation for constructing complex biomacromolecular conjugates.

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Area of Science:

  • Organometallic Chemistry
  • Bioconjugation Chemistry

Background:

  • Organometallic oxidative addition complexes (OACs) are emerging as versatile tools for biomolecule modification.
  • The ability to tune ligand and aryl group properties allows for control over reaction kinetics and regioselectivity, particularly in S-arylation reactions.

Discussion:

  • This study investigates the use of dicyclohexylphosphine-based bidentate P,N-ligated Au(III) OACs for selective S-arylation.
  • Computational and experimental approaches were employed to understand the influence of sterically bulky and electron-deficient aryl substrates on reaction outcomes.
  • A heterotelechelic bis-Au(III) poly(ethylene glycol) (PEG) reagent was synthesized using specific aryl substrates.

Key Insights:

  • The developed Au(III) OACs achieve rapid and regioselective S-arylation of biomolecules.
  • A protein-polymer OAC was formed in situ by reacting the bis-Au(III) PEG with a designed ankyrin repeat protein (DARPin).
  • This intermediate OAC successfully mediated subsequent S-arylation with various small molecules and macromolecules.

Outlook:

  • The presented methodology offers a powerful platform for the rapid synthesis of diverse biomacromolecular heteroconjugates.
  • Future applications may include the facile construction of targeted drug delivery systems and advanced biomaterials.
  • Further exploration of OACs could lead to novel bioconjugation strategies with enhanced efficiency and specificity.