PyAOP CAS: 156311-83-0 from Omizzur 

Peptide synthesis reagents can be broadly divided into carbodiimide type, phosphocation type, urea cation type, imine cation type, organic phosphorus condensation agent, and other types of condensation agents based on their molecular structure. Among them, carbodiimide, urea cation, and phosphorus cation are the three mainstream types of condensation agents. Carbodiimide is the earliest and most commonly used peptide condensation agent, while urea cation and phosphorus cation have the best performance and are widely used.

Phosphorus cation type condensation agent

The discovery of ionic condensation agents, represented by phosphorus cations and urea cations, has enabled the smooth use of non natural amino acids and spatially hindered amino acids in peptide synthesis. They have higher activity and are an important milestone in the development of condensation agents. Phosphorus cation condensation agents have significant advantages over ammonium and urea salts in that they do not react with amino groups and do not terminate peptide chains.

Background

With the emergence of racemic inhibitors, in 1975, Castro designed and synthesized a phosphorus cation based condensation agent BOP (CloP-HOBt) based on HOBt, which attracted people's attention. BOP is a compound that is easy to prepare in large quantities and does not contain crystalline water. It is not only easy to use, but also can significantly improve the condensation reaction rate. Therefore, it is widely used in the solid-phase and liquid-phase synthesis of peptides. However, the byproduct hexamethylphosphoramide generated by BOP in peptide synthesis has carcinogenic toxicity and is not recommended for large-scale production. Inspired by BOP, researchers later developed a byproduct with low toxicity, PyAOP, a condensation agent with relatively higher reactivity.

Although HOBt based phosphonium based condensation agents exhibit excellent performance in the synthesis of ordinary amino acids, they are not satisfactory in the synthesis of amino acids with steric hindrance. For amino acids with high steric hindrance, commonly used peptide coupling reagents such as DCC/HOBt and HOBt based urea salts and phosphate salts have slow reaction rates, are prone to racemization, and side reactions such as the formation of diketopiperazine are prone to occur.

New condensation agent PyAOP

The later development of HOAt based phosphorus cation condensation agents such as AOP, PyAOP, and halogenated phosphorus cation condensation agents such as BOP-Cl, PyCloP, PyBrop, etc. improved this situation and efficiently promoted the formation of amide bonds with steric hindrance For example, in the synthesis of Boc Pro MeVal OMe and Cbz Val MeVal OMe, PyAOP and PyCloP can achieve a yield of 70-85%, while PyBoP can only achieve a yield of 11-26%. The reason for this phenomenon may be that HOBt can form relatively stable active ester intermediates with carboxyl groups, thereby reducing reaction activity and ultimately lowering yield.

PyAOP on Omizzur Ltd

At present, Omizzur provides a large supply of peptide synthesis reagents such as PyAOP. Omizzur has the lowest price and stable quality assurance in the market. Contact Omizzur services for details.

Peptide coupling - PyAOP reagent

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Storage

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