Chinese Journal of Organic Chemistry >
Synthesis and Application of β-Thiolated Amino Acids
Received date: 2023-03-16
Revised date: 2023-04-23
Online published: 2023-05-11
Supported by
National Natural Science Foundation of China(22077080)
Native chemical ligation (NCL) is a milestone reaction in protein chemical synthesis. The NCL involves a reaction between an unprotected peptide with C-terminal thioester and a second unprotected peptide with N-terminal cysteine, which could give a new peptide in a neutral aqueous buffer solution. The cysteine abundance of natural proteins is only 1.7%, which makes it difficult to find suitable cysteine reaction sites and hinders the widespread application of NCL. The “NCL-desulfuri- zation” strategy extended the ligation site to alanine, inspiring chemists to mediate NCL reactions through different types of β-thiolated amino acids. After the NCL is completed, native peptide can be obtained through desulfurization reactions. The “NCL-desulfurization” provides more options for protein synthesis. In recent years, several research groups have completed the synthesis of β-thiolated phenylalanine, leucine, arginine, aspartic acid, asparagine, lysine, methionine, tryptophan, glutamic acid and glutamine, and applied NCL-desulfurization strategy to synthesize proteins. In this article, the synthesis and application of the above β-thiolated amino acids are reviewed.
Haoruo Shangguan , Ping Huang , Zhenya Dai , Ping Wang . Synthesis and Application of β-Thiolated Amino Acids[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3089 -3097 . DOI: 10.6023/cjoc202303023
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