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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Preparation of Alkynes: Alkylation Reaction02:27

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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α-Alkylation of Ketones via Enolate Ions01:10

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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...
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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A Prob(e)able Route to Lysine Acylation.

Gregory R Wagner1, Matthew D Hirschey2

  • 1Duke Molecular Physiology Institute and the Sarah W. Stedman Nutrition and Metabolism Center, Duke University Medical Center, Durham, NC 27701, USA; Department of Medicine, Division of Endocrinology, Metabolism, and Nutrition, Durham, NC 27710, USA.

Cell Chemical Biology
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Summary
This summary is machine-generated.

Protein acylation, a metabolic modification, can be explained by acyl-CoA. Researchers used chemoproteomic probes to show malonyl-CoA-mediated protein malonylation impacts cancer cell glycolysis.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Cancer Research

Background:

  • Protein acylation is a post-translational modification occurring non-enzymatically.
  • Acyl-CoA species, central to intermediary metabolism, are implicated in protein acylation.
  • The specific role of malonyl-CoA in protein malonylation and its cellular consequences remain largely unexplored.

Purpose of the Study:

  • To develop and utilize chemoproteomic probes to investigate protein malonylation.
  • To elucidate the role of malonyl-CoA in mediating protein malonylation.
  • To determine the functional impact of protein malonylation on cellular metabolism, particularly in cancer cells.

Main Methods:

  • Development of novel chemoproteomic probes designed to detect malonylation.
  • Application of these probes in cancer cell models.
  • Analysis of metabolic pathways, specifically glycolysis, affected by malonylation.

Main Results:

  • Successfully developed and validated chemoproteomic probes for studying protein malonylation.
  • Demonstrated that malonyl-CoA actively mediates protein malonylation in cancer cells.
  • Identified that protein malonylation significantly influences the rate and regulation of glycolysis in cancer cells.

Conclusions:

  • Non-enzymatic protein malonylation by malonyl-CoA is a significant metabolic modification.
  • Malonylation plays a regulatory role in cancer cell glycolysis.
  • Chemoproteomic approaches are effective tools for dissecting metabolic modifications and their functions.