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Related Concept Videos

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

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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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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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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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 Acid Anhydrides01:07

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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Related Experiment Video

Updated: Mar 18, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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One Step Synthesis of Inverted Aspartame Type Sweetener, Ac-Phe-Lys, Using Chemically Modified Chymotrypsin.

J Oaki1, K Nakahara, M Tamura2

  • 1a Department of Fermentation Technology, Faculty of Engineering, Hiroshima University.

Bioscience, Biotechnology, and Biochemistry
|July 6, 2016
PubMed
Summary

Chemically modified chymotrypsin enables simplified peptide synthesis, creating Ac-Phe-Lys in one step with a 13% yield. This enzymatic method surpasses traditional approaches for efficient peptide production, especially at scale.

Keywords:
acetyl-phenylalanyl-lysinechemically modified chymotrypsinenzymatic peptide synthesisinverted-aspartame-type sweetenerwater-soluble acylating reagent

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Last Updated: Mar 18, 2026

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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
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Area of Science:

  • Biochemistry
  • Enzymology
  • Chemical Synthesis

Background:

  • Traditional peptide synthesis methods can be complex and time-consuming.
  • Enzymatic synthesis offers a potentially simpler alternative but often faces limitations.
  • Developing efficient enzymatic routes for peptide production is an ongoing challenge.

Purpose of the Study:

  • To explore simplified peptide synthesis techniques.
  • To develop a method for producing the artificial peptide sweetener Ac-Phe-Lys.
  • To evaluate the efficacy of chemically modified chymotrypsin in peptide synthesis.

Main Methods:

  • Preparation of benzyloxycarbonyl chymotrypsin using a water-soluble acylating reagent.
  • Utilizing the modified enzyme for the synthesis of Ac-Phe-Lys.
  • Comparison of the modified enzyme method with native chymotrypsin and chemical synthesis.

Main Results:

  • Chemically modified chymotrypsin enabled direct coupling of Lys with Ac-Phe, forming Ac-Phe-Lys in a single step.
  • The overall yield for Ac-Phe-Lys preparation and purification was 13%.
  • The yield achieved with the modified enzyme is comparable to chemical synthesis methods and superior to native chymotrypsin.

Conclusions:

  • Chemically modified chymotrypsin provides an effective route for simplified peptide synthesis.
  • This enzymatic approach is more efficient than using native chymotrypsin for producing peptides like Ac-Phe-Lys.
  • The method shows promise for large-scale, simplified peptide production.