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Related Concept Videos

Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

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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.
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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EDTA: Auxiliary Complexing Reagents01:26

EDTA: Auxiliary Complexing Reagents

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EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
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Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
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Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
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Torts III01:26

Torts III

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Types of Quasi-intentional Torts in Healthcare
Quasi-intentional torts in healthcare involve acts where intent is not directed to harm an individual but results in harm due to careless or reckless speech.
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Related Experiment Video

Updated: Feb 10, 2026

Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII
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Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

Published on: August 31, 2018

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Organometallic Gold(III) Reagents for Cysteine Arylation.

Marco S Messina1, Julia M Stauber1, Mary A Waddington1

  • 1Department of Chemistry and Biochemistry , University of California, Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States.

Journal of the American Chemical Society
|May 24, 2018
PubMed
Summary

Researchers developed a fast and efficient method for modifying peptides and proteins using gold(III) complexes. This new bioconjugation technique enables the attachment of various molecules, including drugs and fluorescent tags, to cysteine residues.

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Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry
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Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

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Related Experiment Videos

Last Updated: Feb 10, 2026

Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII
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Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry
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Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

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Area of Science:

  • Organometallic Chemistry
  • Bioconjugation Chemistry
  • Medicinal Chemistry

Background:

  • Cysteine bioconjugation is crucial for modifying peptides and proteins.
  • Existing methods often require protection/deprotection steps or harsh conditions.
  • Development of efficient and chemoselective bioconjugation strategies is needed.

Purpose of the Study:

  • To report an efficient method for chemoselective cysteine arylation.
  • To utilize gold(III) organometallic complexes for bioconjugation.
  • To enable modification of unprotected peptides and proteins.

Main Methods:

  • Employing Au(III) organometallic complexes for arylation reactions.
  • Performing bioconjugation under ambient temperature and wide pH range (0.5-14).
  • Synthesizing a library of air-stable Au(III) arylation reagents.

Main Results:

  • Achieved rapid (<5 min) chemoselective cysteine arylation.
  • Demonstrated successful conjugation of diverse molecules: fluorescent dyes, drug molecules, affinity labels, PEG tags, and stapled peptides.
  • Prepared Au(III) arylation reagents as stable, crystalline solids.

Conclusions:

  • The developed method offers a versatile and efficient route for cysteine bioconjugation.
  • Broadens the synthetic scope for modifying complex biomolecules.
  • Provides promising strategies for drug delivery and biomaterial development.