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Bronsted-Lowry Acids and Bases02:58

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The acid-base reaction class has been studied for quite some time. In 1680, Robert Boyle reported traits of acid solutions that included their ability to dissolve many substances, to change the colors of certain natural dyes, and to lose these traits after coming in contact with alkali (base) solutions. In the eighteenth century, it was recognized that acids have a sour taste, react with limestone to liberate a gaseous substance (now known to be CO2), and interact with alkalis to form neutral...
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In 1923, the Brønsted–Lowry definition of acids and bases was proposed by Johannes Brønsted and Thomas Lowry. According to this theory, a Brønsted acid is defined as a species that donates a proton in a chemical reaction and gets converted to its conjugate base. A Brønsted base is defined as a species that accepts a proton in a chemical reaction and gets converted into its conjugate acid. These transfers of protons are caused by the displacement of electrons in these...
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E1 Reaction: Kinetics and Mechanism02:46

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Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
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Relative Reactivity of Carboxylic Acid Derivatives01:13

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Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
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Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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A perspective on cysteine-reactive activity-based probes.

Constantin M Nuber1, Max A Schwab2,3, David B Konrad1,2,3

  • 1Department of Pharmacy, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 Munich, Germany. david.konrad@cup.lmu.de.

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|October 31, 2025
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Summary
This summary is machine-generated.

Activity-based protein profiling (ABPP) uses chemical probes to study protein function and drug mechanisms. This perspective reviews the design and application of covalent cysteine-targeted probes for mass spectrometry-based chemoproteomics.

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Area of Science:

  • Chemical Biology
  • Proteomics
  • Drug Discovery

Background:

  • Activity-based protein profiling (ABPP) is a key chemical biology technique.
  • It enables the investigation of protein function, target identification, and mechanism-of-action studies for chemical probes and drugs.

Purpose of the Study:

  • To provide an overview of covalent cysteine-targeted activity-based probes (ABPs).
  • To discuss the design, application, and future potential of ABPP in chemical biology and pharmaceutical research.

Main Methods:

  • Overview of ABP design, including reactive elements (chemotypes/warheads) and functional handles.
  • Description of mass spectrometry-based chemoproteomics analysis using ABPs.
  • Strategies for developing advanced ABPs for live-cell applications and post-translational modification studies.

Main Results:

  • Covalent cysteine-targeted ABPs are versatile tools for chemical proteomics.
  • Advanced ABPs facilitate live-cell chemoproteomics and the study of post-translational modifications.
  • ABPP holds significant potential for the pharmaceutical industry.

Conclusions:

  • ABPP is a powerful approach for understanding protein function and drug mechanisms.
  • The design and application of advanced ABPs are expanding the reach of chemoproteomics.
  • Further development of ABPP has substantial implications for drug discovery and development.