Synthesis 2016; 48(05): 723-729
DOI: 10.1055/s-0035-1561303
paper
© Georg Thieme Verlag Stuttgart · New York

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

Felix-A. Litty
a  Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical Institute, Christian-Albrechts-University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany
,
Ulrich Girreser
a  Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical Institute, Christian-Albrechts-University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany
,
Bernd Clement
a  Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical Institute, Christian-Albrechts-University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany
,
Dennis Schade*
b  TU Dortmund, Department of Chemistry & Chemical Biology, Otto-Hahn-Straße 6, 44227 Dortmund, Germany   Email: dennis.schade@tu-dortmund.de
› Author Affiliations
Further Information

Publication History

Received: 07 October 2015

Accepted after revision: 02 December 2015

Publication Date:
05 January 2016 (online)


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.

Supporting Information

 
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