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Synthesis 2022; 54(20): 4592-4600
DOI: 10.1055/a-1874-4829
DOI: 10.1055/a-1874-4829
paper
Stereoselective Synthesis of β-Thiolated Aryl Amino Acids
We acknowledge the financial support for this work from Shanghai Pilot Program for Basic Research - Shanghai Jiao Tong University (21TQ1400210), the National Natural Science Foundation of China (22107068, 22077080 and 21907064), and Special Projects of the Central Government in Guidance of Local Science and Technology Development (2021Szvup077).
Abstract
A variety of β-thiolated aryl amino acids were readily synthesized in moderate to excellent yields via 1,4-addition from a readily-accessible thiazoline precursor, which can be prepared from cysteine methyl ester hydrochloride in just three steps. The thiolated products can be subsequently deprotected within one single step in high yields and used directly for subsequent solid-phase peptide synthesis.
Key words
β-thiolated amino acids - Giese reaction - Michael reaction - cysteine surrogates - native chemical ligationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1874-4829.
- Supporting Information
Publication History
Received: 15 May 2022
Accepted after revision: 13 June 2022
Accepted Manuscript online:
13 June 2022
Article published online:
20 July 2022
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