Synthesis and properties of γ-hydroxyarginine

Abstract
Gamma-Hydroxyargi-nine was prepared by 2 methods. In method I, the product of reaction between epichlorohydrin and ethyl sodiomalonate was treated with concentrated NH4OH. Then successively, reaction products were treated with O-methylisourea hydrogen sulfate at pH 11.5, Br, concentrated NH4OH, and trypsin at pH 9.0. In method II, it was prepared by the direct guanidination of gamma-hydroxyomithine. The product was homogeneous as indicated by column chromatography and paper electrophoresis. It was converted to arginine upon reductions with HI and red P, and to gamma-hydroxyomithine upon deguanidation by treatment with Ba(OH)2.

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