Chlorohydroxibenzotriazol CAS NO (26198-19-6) for sale at best price

1. Introduction to Chloro-1-hydroxybenzotriazole (26198-19-6):

Chloro-1-hydroxybenzotriazole, also known as Cl-HOBt, is a valuable reagent in organic synthesis, particularly in peptide coupling reactions and amide bond formation. With its unique chemical structure and reactivity, this compound plays a pivotal role in promoting efficient and selective peptide bond formation while minimizing side reactions.

2. Chemical Composition and Molecular Structure:

Chloro-1-hydroxybenzotriazole is characterized by a benzotriazole core substituted with a chloro (-Cl) group and a hydroxy (-OH) group at adjacent positions. This chemical structure imparts both stability and reactivity to the molecule, making it an effective coupling reagent in peptide synthesis and related organic transformations.

3. Role as a Peptide Coupling Reagent:

Cl-HOBt serves as an efficient peptide coupling reagent, facilitating the formation of peptide bonds between amino acids. Its mechanism involves the activation of carboxyl groups in amino acids, followed by nucleophilic attack by amino groups to generate stable amide linkages. This process occurs under mild conditions, leading to high yields and minimal side reactions.

4. Advantages in Peptide Synthesis:

The use of Cl-HOBt offers several advantages in peptide synthesis, including enhanced reaction kinetics, improved coupling efficiency, and compatibility with a wide range of amino acid derivatives. Its mild reaction conditions minimize racemization and epimerization, ensuring the synthesis of high-quality peptides with high purity and yield.

5. Compatibility with Protecting Groups:

Cl-HOBt exhibits excellent compatibility with commonly used protecting groups, allowing for the synthesis of peptides with diverse structural motifs and functional groups. It enables the incorporation of acid-sensitive and base-labile protecting groups without compromising reaction efficiency or peptide purity, thereby expanding the scope of peptide synthesis strategies.

6. Application in Solid-Phase Peptide Synthesis (SPPS):

Cl-HOBt finds widespread use in solid-phase peptide synthesis (SPPS), where it facilitates the stepwise assembly of peptide chains on solid supports. Its compatibility with resin-bound amino acids and peptide synthesis protocols enables the efficient preparation of peptide libraries, bioconjugates, and peptide mimetics for various biomedical and pharmaceutical applications.

7. Scope in Bioconjugation and Chemical Biology:

Beyond peptide synthesis, Cl-HOBt serves as a valuable tool in bioconjugation and chemical biology applications. It enables the site-specific modification of proteins, peptides, and other biomolecules with diverse functional groups, facilitating the development of bioconjugates for imaging, drug delivery, and diagnostic applications.

8. Mechanism of Activation and Coupling:

The activation mechanism of Cl-HOBt involves the formation of an activated intermediate, where the hydroxy group facilitates carboxyl group activation. Nucleophilic attack by amino groups on the activated intermediate leads to the formation of peptide bonds, accompanied by the release of chloro group as a leaving group.

9. Safety Considerations and Handling:

Cl-HOBt should be handled with caution due to its potential reactivity and toxicity. Proper safety precautions, including the use of appropriate personal protective equipment and adherence to recommended handling procedures, are essential to minimize the risk of exposure and ensure safe laboratory practices.

10. Future Perspectives and Research Directions:

Continued research into the synthesis, optimization, and application of Cl-HOBt and its derivatives holds promise for advancing peptide synthesis, bioconjugation chemistry, and chemical biology. Exploration of novel coupling reagents, reaction methodologies, and peptide assembly strategies may lead to the development of more efficient and versatile synthetic tools for peptide and protein engineering.