Abstract
Triazole groups as biomimetic amide groups in peptides can trigger racemization
Highlights
Amino acids are highly versatile building blocks in organic and bioorganic chemistry
Amino acids are key building blocks for the synthesis of chiral organic materials. In this context, -azido amino acids are interesting starting materials which allow the construction of functionalized, amino-acid based compounds by copper-catalyzed alkyne-azide click reactions. We have employed this strategy for the synthesis of arginine-derivatives and found that the formation of the azide and the click reaction can be carried out in good yields and with almost no loss of stereopurity
While the synthesis of the -azido amino acid and the click reaction itself can be carried out without racemization, the subsequent transformation of the methyl ester into the propargylamide led to significant loss of stereopurity
Summary
Amino acids are highly versatile building blocks in organic and bioorganic chemistry. In this context, -azido amino acids are interesting starting materials which allow the construction of functionalized, amino-acid based compounds by copper-catalyzed alkyne-azide click reactions. We have employed this strategy for the synthesis of arginine-derivatives and found that the formation of the azide and the click reaction can be carried out in good yields and with almost no loss of stereopurity.
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