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Org Lett. 2006 Aug 31;8(18):4035-8.

NG-hydroxyguanidines from primary amines.

Author information

1
Department of Chemistry, University of California-Berkeley, 204 Lewis Hall, Berkeley, CA 94720, USA. nimartin@berkeley.edu

Abstract

A concise and general method for the preparation of N(G)-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N(G)-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 N(G)-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.

PMID:
16928067
DOI:
10.1021/ol061454p
[Indexed for MEDLINE]

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