With the development of biotechnology, the use of peptides in the field of biomedicine is becoming more and more extensive. Protected amino acids for example 20 kinds of standard fmoc amino acids and derivatives are the most basic raw materials for solid phase peptide synthesis technology. Amino acids contain α-amino and carboxyl groups. Some of the 20 amino acids also contain active side chain groups, such as hydroxyl, amino, guanidine and heterocycle.

Both the amino group and the active side chain groups need to be protected in the peptide grafting reaction, and the protective groups are removed after the peptide is synthesized, otherwise the mis-grafting of amino acids and many side reactions will occur. Protected amino acids are generally divided into single-protected amino acids and double-protected amino acids.

What is FMOC Protected Amino Acids?

The reaction principle of FMOC protection of amino acids mainly involves the introduction and removal of amino protecting groups. When synthesizing peptides, FMOC is first reacted with the amino group of amino acids to generate FMOC protected amino acids. This reaction generally uses an organic base as a catalyst and is carried out in an organic solvent.

In the field of peptide synthesis and protein engineering, FMOC (9-fluorenylmethoxycarbonyl) is a very important protecting group used to protect the amino and carboxyl groups of amino acids. The generated FMOC protected amino acids can be used for the synthesis of peptides. When the peptide synthesis is completed, the FMOC protecting group is removed under appropriate reaction conditions to obtain the target peptide or protein.

By using FMOC group to protect amino acids, scientists can effectively prevent amino acids from being modified by external factors during the synthesis process, ensuring that the synthesized peptides and proteins have the correct sequence and stability.

20 Commonly Used Standard Fmoc Amino Acids - Omizzur

>> Click here to view more amino acid catalogs:

      ** Fmoc amino acids                                                           ** Unnatural amino acids

      ** Boc amino acids                                                              ** N-methyl amino acids

      ** Cbz amino acids                                                              ** Peptide reagents & Resins

FAQs 1: What are the Peptide Raw Materials?

The raw materials used for synthesizing peptides by chemical synthesis include starting materials, reagents, and solvents. Their quality, especially the quality of starting materials, will have different effects on the quality of API.

Starting materials mainly refer to protected amino acid derivatives, fatty acids used for peptide chain modification, polyethylene glycol, etc., which are incorporated into the structure of raw materials as important structural fragments, directly affecting the quality of API.

Commonly used amino acid derivatives Commonly used amino acid derivatives include fmoc protected amino acids, boc amino acids, cbz amino acids, unnatural amino acids, N-methyl amino acids, etc.

FAQs 2: Starting Materials for Peptide Synthesis - Standard Fmoc Amino acids

ICHQ11 clearly states that if commercially available chemicals are used as starting materials, applicants generally do not need to justify their rationalization. Commercially available chemicals are usually sold in non-pharmaceutical markets in addition to being used as starting materials for drugs.

Chemical substances prepared by custom synthesis are not commercially available chemicals. Although protected amino acids do not have a non-pharmaceutical market to meet the ICHQ11 definition of commercially available chemicals, they have simple structures, clear chemical properties and structures, are easy to separate and purify, and can be identified and detected using common analytical methods. They have stable chemical properties, are easy to store and transport, and have mature synthetic routes.

Currently, many large international suppliers such as Bachem and Omizzur peptide can continuously produce protected amino acids with stable quality, which are commercially available materials, so standard fmoc amino acids can be identified as starting materials.

FAQs 3: Peptide Chemical Synthesis Method

Chemical synthesis method includes solid phase synthesis method and liquid phase synthesis method. Among them, solid phase synthesis method has significant advantages over liquid phase synthesis method: excess materials can be used for reaction to ensure complete coupling, and excess amino acids, condensing agents, by-products, etc. can be removed by simple washing operations, avoiding complex post-treatment and purification operations, improving production efficiency, etc., so solid phase synthesis method is the most widely used.

Peptide Chemical Synthesis Method VS Biological Fermentation Method

Currently, the methods used to prepare peptide drugs mainly include chemical synthesis method and biological fermentation method. The biological fermentation method is mainly used for the preparation of long peptides. Its advantage is that the production cost is low, but it cannot introduce non-natural amino acids into the peptide sequence, nor can it make various modifications to the peptide chain, so its application is also greatly limited.

FAQs 4: Popular Amino Acid Derivatives: Unnatural Amino acids and Derivatives

Proteins perform a series of significant functions with only 20 natural amino acids. The limited number of functional groups carried by the only 20 natural amino acids cannot meet the needs of protein structure and function in chemical and biological science research and applications.

At present, although the structural modification of proteins has given new functions to natural proteins through chemical modification, gene site-directed mutagenesis and computer-assisted protein design, these methods all rely on the 20 natural amino acids themselves.

In contrast, unnatural amino acids (Unnatural Amino Acids) that can be artificially endowed with diverse functional groups have outstanding performance in protein modification. These unnatural amino acids contain diverse functional groups such as keto, aldehyde, azide, alkynyl, alkenyl, amide, nitro, phosphate, sulfonate, etc., and can undergo a variety of modification reactions, such as: click chemistry, photochemistry, glycosylation, fluorescence color development and other reactions.

The modification of proteins by unnatural amino acids has brought new opportunities for the theoretical study and application of their structure and function. A series of unnatural amino acids have been used for protein modification in bacteria, yeast and mammalian cells with high accuracy and efficiency. Most of them are derivatives of 20 natural amino acids.

The unnatural amino acid derivatives that Omizzur often supplies include phenylalanine derivatives, tyrosine derivatives, glutamine derivatives, alanine derivatives, cysteine derivatives, serine derivatives, lysine derivatives, etc.

FAQs 5: About TSE/BSE Risk Assessment

TSE (Transmissible Spongiform Encephalopathy) is a disease that can cause brain lesions in humans and animals, including Creutzfeldt-Jakob Disease (CJD), variant Creutzfeldt-Jakob Disease (vCJD), Kuru in humans, Bovine Spongiform Encephalopathy (BSE) in cattle, Scrapie in small ruminants (sheep and goats), Chronic Wasting Disease (CWD) in cervids, and Transmissible Mink Encephalopathy (TME) in minks.

Current regulations in many countries require that all licensed drugs must be evaluated for potential risks of transmissible spongiform encephalopathies, including EU Regulation EMA/410/01 "Guidelines for Reducing the Risk of TSE in Human and Veterinary Medicinal Products" and EC No 999/2001 "Rules for the Prevention, Control and Elimination of Certain TSEs", and FDA 21CFR 189.5 "Prohibited Cattle Materials".

The free amino acids used to synthesize protected amino acids may come from the hydrolysis of animal tissue hair, which poses a TES risk. Therefore, the source of the protected amino acids provided by the supplier must be confirmed and the TES risk must be assessed.

Of course, the easier way is to directly purchase non-animal amino acids, and the supplier is required to provide a TSE/BSE statement, which should include "XXX Co., Ltd. hereby certifies that our XXX products meet the following requirements: no animal-derived ingredients; no animal materials from or in contact with affected or quarantined animals that transmit animal spongiform encephalopathy/bovine spongiform encephalopathy. No animals or animal products or animal by-products or veterinary vaccines or animal pathogens are used in our production facilities.

Omizzur Ltd uses total chemical synthesis to produce amino acid derivatives and custom peptide synthesis, which can provide a certificate with the goods.

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