Hydroxybenzotriazole

Hydroxybenzotriazole (HOBt) is a chemical compound commonly used in peptide synthesis to improve the efficiency and yield of amide bond formation. It is a white to off-white crystalline powder with the chemical formula C₆H₅N₃O.

Chemical Properties

Hydroxybenzotriazole is slightly soluble in water and has a melting point of 155-160°C. It is known for its ability to act as a coupling reagent in peptide synthesis, where it helps to activate carboxylic acids for reaction with amines to form peptide bonds.

Applications in Peptide Synthesis

In the field of organic chemistry, HOBt is often used in conjunction with other coupling agents such as dicyclohexylcarbodiimide (DCC) or N,N'-diisopropylcarbodiimide (DIC). The presence of HOBt reduces the formation of side products and racemization, leading to higher purity and yield of the desired peptide.

Mechanism of Action

HOBt works by forming an active ester intermediate with the carboxylic acid group of the amino acid. This intermediate is more reactive towards nucleophilic attack by the amine group of another amino acid, facilitating the formation of the peptide bond. The use of HOBt is particularly advantageous in the synthesis of longer peptides, where the prevention of side reactions is crucial.

Safety and Handling

Hydroxybenzotriazole should be handled with care, as it can be hazardous if ingested or inhaled. Appropriate safety measures, including the use of gloves and eye protection, should be taken when working with this compound.

See Also

• Peptide synthesis
• Dicyclohexylcarbodiimide
• N,N'-diisopropylcarbodiimide
• Amide bond