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NG-Hydroxyguanidines from Primary Amines

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journal contribution
posted on 31.08.2006 by Nathaniel I. Martin, Joshua J. Woodward, Michael A. Marletta
A concise and general method for the preparation of NG-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected NG-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of NG-hydroxy-l-arginine, the intermediate in the enzymatic conversion of l-arginine to nitric oxide and l-citrulline by nitric oxide synthase.