Peptide solid-phase synthesis method—Fmoc method and Boc method

Peptide synthesis not only has important theoretical significance, but also has important application value. New peptide structures can be verified through peptide synthesis; new peptides can be designed to study the relationship between structure and function; provide important information for the reaction mechanism of peptide biosynthesis; establish model enzymes and synthesize new peptide drugs. In 1963, RB Merrifield created a solid-phase synthesis method that fixes the amino acids at the carboxyl end of the peptide to an insoluble resin, and then sequentially couples the amino acids to this resin to extend the peptide chain and synthesize the peptide. Need to simply wash the resin, you can achieve the purpose of purification. It overcomes the difficulty of purifying each step of the product in the classical liquid-phase synthesis method, laying a foundation for the automated synthesis of peptides. For this, Merrifield won the 1984 Nobel Prize in Chemistry.

The Boc synthesis method established by Merrifield uses TFA (trifluoroacetic acid) -removable Boc (tert-butoxycarbonyl) as the α-amino protecting group, and the side chain protection uses benzyl alcohols. During the synthesis, a Boc-amino acid derivative is covalently cross-linked to the resin. Boc is removed by TFA, the free amino terminal is neutralized with triethylamine, and then the next amino acid is activated and coupled by DCC. HF method or TFMSA (trifluoromethanesulfonic acid) method. The Boc method has successfully synthesized many biological macromolecules, such as active enzymes, growth factors, and artificial proteins.

In the Boc synthesis method, the acid is used to deprotect repeatedly. This treatment brings some problems: for example, at the junction of the peptide and the resin, when each 50% TFA is used to remove the Boc group, there are about 1.4% of the peptide Shedding from the resin, the longer the synthetic peptide chain, the more serious this loss; in addition, acid treatment will cause some side reactions of the side chain, the Boc synthesis method is particularly unsuitable for the synthesis of peptides containing tryptophan and other acid unstable . In 1978, Chang, Meienlofer and Atherton et al. Successfully used the Fmoc (9-fluorenylmethoxycarbonyl) group reported by Carpino as the α-amino protecting group to successfully carry out Fmoc solid-phase synthesis of peptides. The fundamental difference between the Fmoc method and the Boc method is that the Fmoc that can be removed by the base is an α-amino protecting group, the side chain is protected by TFA-removable tert-butoxy, etc. The resin is 90% TFA-cleavable Alkoxybenzyl alcohol type resin, the final deprotection avoids strong acid treatment.

Since Merrifield has successfully developed the solid-phase peptide synthesis method, after continuous improvement and perfection, the solid-phase method has become a commonly used technology in the synthesis of peptides and proteins, showing the advantages that the liquid-phase synthesis method cannot compare with. In recent decades, solid-phase synthesis of peptides has become a conventional method of peptide synthesis due to its outstanding advantages of time-saving, labor-saving, material-saving, computer control, and popularization. Various peptide automatic synthesizers based on the two methods of Boc and Fmoc have also appeared one after another, and are still being developed and improved continuously.

Cali-Bio has the most advanced technology and process in the peptide synthesis process. It has successfully synthesized tens of thousands of high-purity peptides for many scientific research institutions, colleges and biological companies in the United States, which are used in antibody preparation, drug development and Various fields such as the development of peptide vaccines. Cimejet introduced Cali-Bio's peptide synthesis service to China, and combined with China's national conditions, it aims to provide Chinese customers with special services for the quality of peptide synthesis abroad and enjoy domestic synthesis prices. In order to give back to our customers' support for Simex products and services, we now provide a 15% discount on Cali-Bio peptide synthesis services in the United States! Can provide solid phase / liquid phase synthesis of linear, cyclized peptides. For details, please click: Peptide Synthesis-Cali-Bio Peptide Synthesis Service in the United States 15% off special offer!

If you are interested in the above peptide synthesis services, please contact / 9569/8795/4237 to Ximeijie Technology Co., Ltd. (Shanghai please / 63599872 to Ximeijie Shanghai Branch) to inquire about the related custom synthesis services, we will provide you with After completing the order, Ximeijie will do more for you!

Peptide solid-phase synthesis—Fmoc method and Boc method

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