An Efficient Synthesis of Optically Pure N ^δ-Monomethylated l-Arginine and l-Ornithine

Abstract

N ^ω-Methylated l-arginines such as asymmetric dimethyl-l-arginine (ADMA) and monomethyl-l-arginine (NMMA) are well-known endogenous modulators of the nitric oxide (NO) generating system. To understand the (patho)physiological role and impact of N ^δ-methylation of l-arginine and l-ornithine an efficient synthesis of the pure enantiomers was needed. A synthetic approach that furnished both the desired amino acids in 8–10 steps from commercially available N-Boc-l-ornithine in good overall yields (20–21%) and with high optical purity (>99% ee) is reported.

Key words

alkylation - amino acids - bioorganic chemistry - chiral pool - chiral resolution - protecting groups

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