- Solid phase peptide synthesis is SPPs. R. Bruce Merrifield, who has made a breakthrough in peptide synthesis technology, designed a peptide synthesis pathway and named it solid phase synthesis pathway.
- olid phase peptide synthesis is abbreviated as SPPs
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Solid phase peptide synthesis is SPPs. R. Bruce Merrifield, who has made a breakthrough in peptide synthesis technology, designed a peptide synthesis pathway and named it solid phase synthesis pathway.
R. Bruce Merrifield won the Nobel Prize in 1984 for his contribution to peptide synthesis.
Peptide synthesis research has gone through a glorious course of more than 100 years. In 1902, Emil Fischer first began to pay attention to peptide synthesis. Due to the lack of knowledge in peptide synthesis at that time, the progress was also quite slow. Until 1932, Max Bergmann and others began to use benzyloxycarbonyl (z) to protect α – amino groups, peptide synthesis began to have certain development.
In the 1950s, organic chemists synthesized a large number of bioactive peptides, including oxytocin, insulin, etc., and also made many achievements in peptide synthesis methods and amino acid protection groups, which provided practical and theoretical basis for the emergence of solid-phase synthesis methods.
In 1963, Merrifield first proposed solid-phase peptide synthesis (SPPs). As a milestone in peptide chemistry, SPPs has become the preferred method for peptide synthesis because of its convenient and rapid synthesis. Moreover, it has brought about a revolution in the organic synthesis of polypeptides and has become an independent discipline solid phase organic synthesis (SPOS). Therefore, Merrifield won the Nobel Prize in chemistry in 1984.
After repeated screening, Merrifield finally abandoned the use of benzyloxycarbonyl (z) in solid phase. First, tert butyloxycarbonyl (BOC) was used to protect α – amino groups and used in solid-phase peptide synthesis. At the same time, Merrifield invented the first peptide synthesis instrument in the late 1960s, and synthesized biological protease, ribonuclease (124 amino acids) for the first time.
In 1972, Lou carpino first used 9-fluorene methoxycarbonyl (Fmoc) to protect α – amino group. It can be quickly removed under alkaline conditions and the reaction can be completed in 10 minutes. Moreover, due to its mild reaction conditions, it has been widely used rapidly. Various peptide automatic synthesis instruments based on BOC and Fmoc methods have also appeared and developed, and are still being improved and improved. At the same time, solid-phase synthesis resin, peptide condensation reagents and amino acid protection groups, including the synthesis of cyclic peptide amino acid orthogonal protection has also achieved fruitful results.
olid phase peptide synthesis is abbreviated as SPPs
The simple process of solid phase peptide synthesis (the process of synthesizing a dipeptide) is given below.
Chloromethyl polystyrene resin, as an insoluble solid-phase carrier, first covalently linked an amino acid protected by a blocking group (x in the figure) to the solid-phase carrier. In the presence of trifluoroacetic acid, the amino group is removed, and the first amino acid is attached to the solid phase carrier. Then the carboxyl group of the second amino acid blocked by amino group is activated by N, n ˊ – Dicyclohexylcarbodiimide (DCC). The second amino acid activated by DCC reacts with the amino group of the first amino acid connected to the solid-phase carrier to form a peptide bond, thus forming a dipeptide with a protective group on the solid-phase carrier.
Repeat the above peptide bond formation reaction to make the peptide chain grow from C-terminal to N-terminal until the desired peptide chain length is reached. Finally, the protective group X was removed and the ester bond between the peptide chain and the solid carrier was hydrolyzed with HF to obtain the synthetic peptide.
The advantage of solid phase synthesis is that the initial reactants and products are connected to the solid carrier, so all reactions can be carried out in one reaction vessel, which is convenient for automatic operation. Adding excessive reactants can obtain high yield products, and the products are easy to be separated.
Chemical synthesis of peptides can now be carried out on a programmed automated peptide synthesizer. Merrifield successfully synthesized bradykinin (9 peptide) and ribonuclease with 124 amino acid residues. In September 1965, Chinese scientists synthesized bovine insulin for the first time in the world.
In the field of tobacco control active peptides, the solid-phase synthesis method is used to synthesize the smoking cessation peptides, repair peptides and hydrolyzed peptides to make the peptide chain grow from the C-terminal to the N-terminal.
The polymer solution of the active peptides has the functions of detoxification and quitting, reducing the amount of smoke, repairing the damage, reducing the relapse and decomposing the second-hand smoke poison. It can be activated by the active PP and improve the effect of the active peptide. It is called the smoke control nuclear bomb.
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