Abstract
A new synthetic strategy to alkylate amino groups under mild conditions has been developed. It utilizes only 4 Å molecular sieves as base in order to promote the N-alkylation reaction, in presence of the appropriate alkyl halide. The methodology was validated by the simple and efficient side-chain N-alkylation of o-Ns-protected Fmoc-amino acid. One of them was introduced as building block into a peptide sequence, thus allowing the preparation of site-specific alkylated peptide molecules.
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Our thanks to Mr. Leopoldo Zona for technical assistance with NMR experiments.
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Monfregola, L., De Luca, S. Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves. Amino Acids 41, 981–990 (2011). https://doi.org/10.1007/s00726-010-0798-6
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DOI: https://doi.org/10.1007/s00726-010-0798-6