Synthesis, purification, and characterization of Fmoc-(Dmb)Xxx-OH protected amino acids (Xxx = Ala, Leu) was performed. N-Dmb protection was accomplished via reductive amination of 2,4-dimethoxybenzaldehyde with selected L-amino acids. Isolated yields after flash chromatography over silica gel were 47-76 % (Compounds 2 a,b). N-Dmb protected amino acids were subsequently Fmoc protected using an excess of an Fmoc-OSu and extended reaction times (e.g., 24 hours). Isolated yields after flash chromatography over silica gel were ~ 75 % (Compounds 3 a,b). All protected amino acids were characterized using 1H and 13C NMR spectroscopy. Protected amino acids are now being utilized as building blocks in solid-phase peptide synthesis. (Dmb = Dimethoxybenzyl, Fmoc = Fluorenylmethyloxycarbonyl)

Synthesis of amide N-H protected amino acids for use in solid phase peptide synthesis

248th National Meeting (2014)

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