Protected Amino Acids / Alfa Chemistry
Introduction To Amino Acid Side Chain Protecting Groups
Introduction To Amino Acid Side Chain Protecting Groups
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Introduction To Amino Acid Side Chain Protecting Groups

In peptide synthesis, the active side chain groups of some amino acids also need to be protected. The following are commonly used protecting groups for different amino acid side chains and their removal conditions.

Amino acidSide chain groupProtecting groupRemoval condition
Aspartic acid (Asp)Carboxylt-ButylTFA, TMSBr
Cycloalkanol esters, adamantyl estersTMSOTf
Glutamic acid (Glu)Carboxylt-ButylTFA, TMSBr
Cycloalkanol esters, adamantyl estersTMSOTf
Serine (Ser)Hydroxylt-ButylTFA, TMSBr
Threonine (Thr)Hydroxylt-ButylTFA, TMSBr
Tyrosine (Tyr)Hydroxylt-ButylTFA, TMSBr
Asparagine (Asn)Amino9-Xanthenyl, 2,4,6-trimethoxybenzyl, TrtTFA
Glutamine (Gln)Amino9-Xanthenyl, 2,4,6-trimethoxybenzyl, TrtTFA
Histidine (His)ImidazolylBocTFA
Cysteine (Cys)Sulfydrylp-Methylbenzyl, p-methoxybenzyl, diphenylmethylTFA
BenzylNa/NH3
Arginine (Arg)GuanidylAlkoxycarbonyl, sulfonyl, TrtTFA
Lysine (Lys)AminoAcyl, benzyloxycarbonyl, BocTFA