Related Experiment Video
Updated: May 25, 2026
09:39
Targeted Antibody Blocking by a Dual-Functional Conjugate of Antigenic Peptide and Fc-III Mimetics (DCAF)
Published on: September 17, 2019
Simplifying native chemical ligation with an N-acylsulfonamide linker
Fabienne Burlina1, Caroline Morris, Raymond Behrendt
1UPMC Univ Paris 06, CNRS, ENS, UMR 7203 Laboratoire des Biomolécules, 4 place Jussieu, 75005 Paris, France.
Chemical Communications (Cambridge, England)
|February 1, 2012
Summary
A new sulfamylbutyryl linker simplifies peptide chemical ligation. This method offers reaction speeds comparable to native chemical ligation, enhancing peptide synthesis efficiency.
Area of Science:
- Biochemistry
- Organic Chemistry
- Synthetic Chemistry
Background:
- Chemical ligation is a key method for synthesizing peptides and proteins.
- Existing methods can be complex or require harsh conditions.
Purpose of the Study:
- To develop a simplified and efficient chemical ligation procedure for peptides.
- To introduce the sulfamylbutyryl linker as a novel activating group.
Main Methods:
- Utilized a sulfamylbutyryl linker as a mildly activating group.
- Performed direct addition of peptidyl N-methylsulfonamide with excess thiols.
Main Results:
- Achieved a simplified procedure for peptide chemical ligation.
- Demonstrated reaction speeds comparable to native chemical ligation.
- The sulfamylbutyryl linker proved effective in facilitating ligation.
Conclusions:
- The sulfamylbutyryl linker provides a straightforward approach to peptide ligation.
- This method enhances the efficiency and accessibility of peptide synthesis.
- The procedure is a valuable addition to the toolkit for peptide chemists.
Related Concept Videos
01:19Amines to Amides: Acylation of Amines
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 amide...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
01:19Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme activation, sulfur...
00:55Nitriles to Amines: LiAlH4 Reduction
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
01:07Acid 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...
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...
02:27Preparation of Alkynes: Alkylation Reaction
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.
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.