Concise synthesis of both diastereomers of 3-hydroxy-L-arginine

The hydroxylated amino acid 3-hydroxy-L-arginine is an intermediate in the biosynthesis of the non-proteinogenic amino acid capreomycidine and possibly also of its epimer epicapreomycidine. The novel concise synthesis of 3-hydroxy-L-arginine presented here allows the efficient preparation of both 3-epimers of this beta-hydroxy amino acid. It also offers the potential to obtain suitably isotope-labelled derivatives for the elucidation of epicapreomycidine assembly in the biosynthesis of complex natural products. (C) 2009 Elsevier Ltd. All rights reserved.