Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves.
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.
Institute of Biostructures and Bioimages, National Research Council, 80138, Naples, Italy.
Luca
L
Monfregola
Stefania
S
De Luca
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides