Deprotection Of Protected Amino Acids

During the chemical synthesis of peptides, it is usually required that the protecting groups of protected amino acids can be completely and quantitatively removed after synthesis. When several protecting groups need to be removed at the same time, it is very effective to use the same protecting group to protect different functional groups (for example, a benzyl group can protect a hydroxyl group as an ether, an acid as an ester, and an amino group as a carbamate). When you want to selectively remove a protecting group, you can only use different types of protecting groups (for example, a Cbz-protected amino group can be removed by hydrogenolysis, but another Boc-protected amino group is stable). In addition, the impact on the removal rate of protecting groups must be considered from electronic and stereoscopic factors (for example, tertiary alcohol esters of carboxylic acids are much more difficult to remove than primary alcohol esters). Alfa Chemistry masters the deprotection strategies of various protecting groups and can remove the protecting groups of protected amino acids with various complex structures during synthesis reactions to assist your scientific research.

Our Services

We provide our customers with deprotection services for protected amino acids, including the removal of single protecting groups and multiple protecting groups. Common deprotection services include:

• Removal of 9-fluorenylmethyloxycarbonyl (Fmoc)
• Removal of tert-butyloxy carbonyl (Boc)
• Removal of carbobenzoxy (Cbz)
• Removal of acetyl (Ac)
• Removal of benzoyl (Bz)
• Removal of benzyl (Bzl)
• Removal of dabsyl (Dbs)
• Removal of 2,4-dinitrophenyl (Dnp)
• Removal of dansyl (Dns)
• Removal of 2-nitrophenylsulfenyl (Nps)
• Removal of phenylthiohydantoin (PTH)
• Removal of allyloxycarbonyl (Alloc)
• Removal of trimethylsilyl ethoxycarbonyl (Teoc)
• Removal of trityl (Trt)

• Removal of phthalyl (Phth)
• Removal of trifluoroacetyl (Tfa)
• Removal of 2,2,2-trichloroethoxycarbonyl (Troc)
• Removal of p-methoxybenzyl (PMB)
• Removal of acetamidomethyl (Acm)
• Removal of methoxybenzyl (Mob)
• Removal of 2,4-Dimethoxybenzyl (Dmb)
• Removal of Allyl
• Removal of methyl esters
• Removal of ethyl esters
• Removal of benzyl esters
• Removal of succinimidyl esters
• Removal of tert-butyl esters
• ...

Our Deprotection Strategies

We have a variety of deprotection strategies for different protecting groups. Specific protecting groups protecting amino acids can be removed for you based on your needs. Below are some of our common deprotection strategies.

• Catalytic hydrogenolysis. Taking the deprotection of Cbz protecting group as an example. It often uses hydrogen as the hydrogen donor and Pd-C as the catalyst to remove it at normal temperature and pressure. In addition, catalytic hydrogenolysis is also commonly used to remove Bn and PMB protecting groups.
• Acidolysis. This strategy usually removes specific protecting groups under acidic conditions such as trifluoroacetic acid, hydrochloric acid, and hydrofluoric acid.  Taking the deprotection of Boc protecting group as an example, the most commonly used method is to use trifluoroacetic acid or trifluoroacetic acid/dichloromethane (1:1, v/v) solution, which can be deprotected quickly at room temperature.
• Alkaline deprotection. This strategy generally removes specific protecting groups under alkaline conditions such as NH₃, Et₃N, 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (DBU), piperidine, ethanolamine, cyclohexylamine, morpholine, sodium carbonate, and sodium hydroxide. For example, the removal of Fmoc protecting groups often uses simple amine bases to deprotect through alkaline β-elimination reactions.
• In addition, reductive deprotection, oxidative deprotection, etc. are also commonly used deprotection strategies. We will choose the corresponding deprotection method according to the specific protecting group.