Synthesis of N-α-Fmoc-N-ε-Tetrabutyl Ester-EDTA-L-lysine: An Amino Acid Analog to Prepare Affinity Cleaving Peptides

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Abstract
Synthesis of an amino acid analog. N-α-Fmoc-N-ε-tetrabutyl ester EDTA-L-Lysine, suitable for incorporating a strong metal binding site at any internal sequence position in a peptide is described. To overcome the solubility and purification problems during the synthesis, we prepared esters of N-α-Fmoc-N-ε-Boc-L-Lysine. Since the t- butyl group on the amino acid is acid labile and Fmoc group at α-amino group is base sensitive, protection of N-α-Fmoc-N-ε-Boc-L-Lysine requires an ester that can be prepared and removed under neutral conditions. A scheme for selective protection and deprotection of lysine is reported.