N^G-Hydroxyguanidines from Primary Amines

Nathaniel I. Martin,* Joshua J. Woodward and Michael A. Marletta

*Department of Chemistry, University of California Berkeley, 204 Lewis Hall, Berkeley, California 94720, Email: nimartinberkeley.edu

N. I. Martin, J. J. Woodward, M. A. Marletta, Org. Lett., 2006, 8, 4035-4038.

DOI: 10.1021/ol061454p (free Supporting Information)

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Abstract

Primary amines are converted to protected N^G-hydroxyguanidines in a one-pot procedure using readily prepared materials. 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, is described.

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Key Words

Guanidines

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ID: J54-Y2006-2510