Differences of peptide coupling reagents (Details)

Peptide coupling reagents is the key chemical reagent to construct amide bond in peptide synthesis. This article about peptide coupling reagents introduction is about 1300 words, suggest scientific research friend collection. 

Peptide is a kind of compound with molecular weight between protein and amino acid, which is formed by the connection of multiple amino acids through peptide bond (i.e. amide bond). At present, the development of peptide drugs has become an indispensable and important field of modern drug research and development. Chemical synthesis is an important way to synthesize peptides. In this paper, peptide condensation reagent is a kind of special chemical reagent which is essential to construct amide bond in peptide chemical synthesis.

At present, there are many kinds of commercial peptide coupling reagents on the market, so it is not easy to choose a suitable one. From the point of view of molecular structure, we can divide them into three types: carbodiimide type, phosphorus positive ion type and urea positive ion type.

Carbodiimide type is the earliest and most commonly used peptide condensing agent, while urea cation type has more excellent properties in peptide synthesis. It has become the mainstream peptide coupling reagents in scientific research.

1. Carbodiimide

This type contains N = C = N functional group, which is usually prepared from thiourea dehydrogenation of hydrogen sulfide or urea dehydrogenation and hydrolyzed to urea derivatives. It is mainly used to activate carboxyl groups and promote the formation of amides and esters. Carbodiimide can also react with amine to form guanidine. This kind of condensation agent has the advantages of fast reaction speed, high yield, mild reaction conditions and simple synthesis.

DCC CAS： 538-75-0

DIC CAS： 693-13-0

EDC CAS: 1892-57-5

CDI CAS: 530-62-1

HOBt:   2592-95-2   

HOOBt :  28230-32-2   

Cl-HOBt: 26198-19-6

HOAt:   39968-33-7  

HOSu（NHS）: 6066-82-6

2. Phosphinium

Compared with carbodiimide type, phosphine positive ion type has more excellent performance in peptide synthesis of common amino acids. However, the onium salts developed based on HOBt often produce explosive by-products in the reaction, which brings great potential for normal use.

BOP   CAS:56602-33-6 

PyBOP  CAS：128625-52-5

PyAOP  CAS: 156311-83-0  

PyBrOP CAS:132705-51-2 

3. Uroniums

HBTU is a kind of urea cationic condensing agent based on HOBt, and a series of cationic reagents such as HOBt and hoat have been developed rapidly. This kind of highly efficient condensing agent based on HOBt and hoat can effectively promote the formation of sterically hindered amide bond, and has the advantages of fast reaction speed, small racemization and high yield. Generally speaking, it is the mainstream peptide condensation reagent in the current market. The disadvantage is that the condensation agent and the amino component will synthesize the corresponding guanidine derivatives.

Uroniums type of coupling reagents：

TBTU 125700-67-6     

HBTU 94790-37-1 

HATU 148893-10-1

TATU        

TCTU 330641-16-2       

HCTU 330645-87-9

TDBTU 125700-69-8        

TSTU

4.Other coupling reagents

EEDQ  CAS:16357-59-8

BOP-Cl: CAS:68641-49-6

EEDQ:  16357-59-8

DMAP:  1122-58-3

DEPBT:  165534-43-0

4,5-Dicyanoimidazole: CAS:1122-28-7

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