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Related Concept Videos

α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the strong interaction...
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...

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Determination of the Gas-phase Acidities of Oligopeptides
11:00

Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

Aldehyde complexes with protonated peptides in the gas phase.

Xiangguo Shi1, Jianhua Ren, Joel H Parks

  • 1Rowland Institute at Harvard, 100 Edwin H. Land Boulevard, Cambridge, Massachusetts 02142, USA.

The Journal of Physical Chemistry. B
|August 13, 2011
PubMed
Summary

Aldehyde complexes with peptide ions form through gas-phase collisions, requiring water vapor for stability. Complex formation kinetics reveal competition between conformers, with proton transfer driving complex dissociation.

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Area of Science:

  • Analytical Chemistry
  • Physical Chemistry
  • Biochemistry

Background:

  • Peptide ions are crucial in biological systems and analytical chemistry.
  • Understanding ion-ligand interactions is key to mass spectrometry applications.
  • Aldehydes play diverse roles in biological processes and chemical synthesis.

Purpose of the Study:

  • To investigate the formation and stability of gas-phase aldehyde-peptide complexes.
  • To elucidate the kinetics and mechanisms governing aldehyde binding to peptide ions.
  • To explore the role of water vapor and structural heterogeneity in complex formation.

Main Methods:

  • Electrospray ionization (ESI) for generating desolvated peptide ions.
  • Radio frequency (RF) ion trap for ion storage and bimolecular collisions.
  • Mass spectrometry (MS) for analyzing aldehyde-peptide complex formation and dissociation.

Main Results:

  • Stable aldehyde-peptide complexes require the presence of water vapor for formation.
  • Complex formation kinetics exhibit multiexponential time dependence, indicating structural heterogeneity.
  • Aldehyde binding involves competition between different peptide conformers.
  • Proton transfer to the aldehyde ligand is the primary pathway for complex loss.

Conclusions:

  • Water vapor is essential for the stability of gas-phase aldehyde-peptide complexes.
  • The kinetics of complex formation are influenced by peptide structural heterogeneity and conformer competition.
  • Proton transfer mechanisms dictate the dissociation pathways of these complexes.