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Abstract
Synthesis of N-formyl amino acids and peptides, that play a crucial role in protein biosynthesis and for the development of antimicrobial peptides, faces many challenges including harsh reaction condition, biproduct management etc. Reported here, is an efficient peroxide mediated N-formylation of amino acid ester derivatives via radical decarboxylative coupling with glyoxylic acids where only water and carbon dioxide forms as biproduct. H2O2 works well with N-substituted while TBHP was successful for the N-formylation unprotected amino acid esters and oligopeptides. The methodology was extended for the synthesis of bioactive N-formyl methionine and f-MLP. The library of synthesised N-ferrocenyl as well as free N-formyl amino acid and peptide derivatives might serve as hybrid material for medicinal and electrochemical applications
Supplementary materials
Title
N-formylation of amino acid esters and peptides via peroxide mediated decarboxylative C-N coupling with α-keto acids
Description
A simple, convenient, and mild method for the N-formylation of amino acids and peptides was achieved through peroxide-mediated decarboxylative coupling of amino acids with alpha-keto acids. This metal and coupling reagent-free condition enables only water or tertiary butanol and carbon dioxide as the easily removable byproducts. The developed methodology gives access to a library of synthetically relevant N-formyl amino acid derivatives, peptides, and their ferrocene conjugates, including chemotactic agents N-formyl methionine and f-MLP, that can display interesting pharmaceutical and electrochemical applications.
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