Peptidecoupling mechanism N,N'-Diisopropylcarbodiimide, commonly known as DIC, is a vital coupling reagent widely employed in peptide synthesis. Its primary function is to facilitate the formation of amide bonds between amino acids, a fundamental step in constructing peptides and proteinsN,N'-Diisopropylcarbodiimide (DIC)Peptide synthesis· Main Properties · Product Specification. Colorless to pale yellow mass, Complying. Identity (GC) .... DIC offers several advantages over other carbodiimides, particularly in solid-phase peptide synthesis, due to the solubility characteristics of its urea byproduct. This makes it a preferred choice for many researchers aiming to efficiently create complex peptide chains.
The core of peptide synthesis involves linking the carboxyl group of one amino acid to the amino group of another. This reaction, however, is not spontaneous and requires activation. Carbodiimides like DIC act as activating agents. They react with the carboxyl group of an amino acid, forming a highly reactive O-acylisourea intermediate. This intermediate is then susceptible to nucleophilic attack by the amino group of the subsequent amino acid, leading to the formation of a peptide bond and the release of N,N'-diisopropylurea as a byproduct.StandardCouplingProcedures: Converting CHA and DCHA Salts to Free Acids. For stability considereations and easier handling, some N-protected amino acids are ...
The mechanism involves:
1. Activation of the Carboxyl Group: DIC reacts with the carboxylic acid of the first amino acid.
2. Formation of the O-acylisourea: This creates a reactive intermediate.
3.DIC purum, = 98.0 GC 693-13-0 Nucleophilic Attack: The amino group of the second amino acid attacks the activated carboxyl group.
4. Peptide Bond Formation: The peptide bond is formed, and N,N'-diisopropylurea is released.
While other carbodiimides like DCC (N,N'-Dicyclohexylcarbodiimide) are also used in peptide synthesis, DIC often proves more amenable to solid-phase peptide synthesis (SPPS). In SPPS, the growing peptide chain is attached to a solid support, and reagents are washed away after each stepAutomatic procedures for the synthesis of difficult peptides .... The key advantage of DIC here is that its urea byproduct, N,N'-diisopropylurea, is soluble in common organic solvents used in SPPS. This solubility ensures that the byproduct is easily washed away, preventing its accumulation and potential interference with subsequent reactions.Coupling Reagents In contrast, the urea byproduct from DCC is less soluble, which can complicate purification and lead to lower yields or purityDICis used instead in solid phasesynthesissince the urea byproduct is more soluble and will remain in solution. In certain applications, such as modifying ....
DIC is part of a broader family of carbodiimides used in organic synthesis, including DCC and EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide)DICis used as apeptidecoupling reagent in thesynthesisof: two protectedpeptideproteins of scorpion neurotoxin II; the N-hydroxysuccinamide active .... Each has specific applications and properties.
* DCC: Historically significant, but its insoluble urea byproduct (DCU) can be problematic in SPPS.
* EDC: Water-soluble, making it useful for solution-phase peptide synthesis and bioconjugation reactions in aqueous buffers.
* DIC: Favored for SPPS due to its soluble urea byproduct, offering ease of handling and efficient removalDiisopropylcarbodiimide.
DIC is often used in conjunction with additives like HOBt (1-Hydroxybenzotriazole) or Oxyma Pure (Ethyl cyanohydroxyiminoacetate).2023年5月4日—Diisopropylcarbodiimide (DIC) constitutes one of the most widely used coupling reagents for amide bond formation inpeptide synthesis. These additives help to suppress side reactions, such as epimerization (racemization of chiral centers in amino acids), thereby improving the stereochemical integrity and purity of the synthesized peptide. The combination of DIC with additives like Oxyma Pure is particularly noted for its efficiency and cost-effectiveness in synthesizing challenging peptide sequences.
Beyond standard peptide synthesis, DIC finds application in the synthesis of various modified peptides, peptide conjugates, and complex biomolecules. Its reliability and efficiency make it a go-to reagent for both academic research and industrial production.
When using DIC, several factors need consideration:
* Purity: High purity DIC (e.gIn organic chemistry,peptide synthesisis the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as ...., ≥98.Epimerisation in Peptide Synthesis - PMC - PubMed Central0% GC) is essential for reproducible and successful synthesis.作者：A Caporale·2018·被引用次数：54—A systematic study for optimizing yield and purity of so-called difficult sequences using oxyma/DICas first choice cheapcouplingagent. · Morpholine/DBU are ...
* Additives: The choice of additive (HOBt, Oxyma Pure, HOAt) can significantly impact reaction efficiency and minimize epimerization, especially for sensitive amino acid residues.
* Solvents: Appropriate solvents are crucial for both reagent solubility and byproduct removal.
* Safety: Like many organic reagents, DIC requires careful handling, with appropriate personal protective equipment and ventilation.
In conclusion, N,N'-Diisopropylcarbodiimide (DIC) stands as a cornerstone reagent in modern peptide synthesis, particularly within the robust framework of solid-phase peptide synthesis2024年6月4日—Peptide coupling is the process of joining two amino acids to form a peptide bond, a crucial step inpeptide synthesis.. Its ability to efficiently facilitate amide bond formation, coupled with the advantageous solubility of its urea byproduct, makes it an indispensable tool for chemists constructing peptides for therapeutic, diagnostic, and research purposes.
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