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Synthesis Of 15Nω‐Hydroxy‐L‐arginine And ESR And 15N‐NMR Studies For The Elucidation Of The Molecular Mechanism Of Enzymic Nitric Oxide Formation From L‐Arginine

B. Clement, E. Schnörwangen, T. Kaempchen, P. Mordvintcev, A. Mülsch
Published 1994 · Chemistry, Medicine

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Nω‐Hydroxy‐L‐arginine (2) was prepared by a multi‐stage synthesis; the key step was the addition of hydroxylamine to the protected cyanamide 8. The presence of N‐hydroxyguanidines was confirmed, above all, by 15N‐NMR investigations. 15Nω‐Hydroxy‐L‐arginine (2) was converted quantitatively to 15NO by NO synthases from macrophages. 15NO was identified by ESR‐spectroscopy. These experiments confirm that 15Nω‐hydroxy‐L‐arginine (2) is an intermediate in the biosynthesis of NO from arginine (1) and that the N‐hydroxylated N‐atom is present in the NO formed.
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