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Synthesis 2016; 48(05): 723-729
DOI: 10.1055/s-0035-1561303
DOI: 10.1055/s-0035-1561303
paper
An Efficient Synthesis of Optically Pure N δ-Monomethylated l-Arginine and l-Ornithine
Weitere Informationen
Publikationsverlauf
Received: 07. Oktober 2015
Accepted after revision: 02. Dezember 2015
Publikationsdatum:
05. Januar 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201605/lookinside/thumbnails/ss-2015-z0587-op_10-1055_s-0035-1561303-1.jpg)
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 groupsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561303.
- Supporting Information
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