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Synthesis 2011(15): 2357-2368  
DOI: 10.1055/s-0030-1260100
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of N-Alkyl-N-hydroxyguanidines: A Comparative Study Using Different Protecting Group Strategies

Oliver Ries, Anne Ochmann, Christian Ducho*
Georg-August-University Göttingen, Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)399660; e-Mail: cducho@gwdg.de;
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Publication History

Received 20 May 2011
Publication Date:
08 July 2011 (online)

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Abstract

Representing a prime example of the interesting structures found in natural products, the N-alkyl-N-hydroxyguanidine moiety has so far only found limited attention in synthetic organic chemistry. Our studies on Streptomyces-produced muraymycin nucleoside antibiotics have led to a systematic investigation of the synthetic access to the N-hydroxyguanidine-functionalized lipid structure of biologically potent A-series muraymycins. A protecting-group-free approach has been proven to be superior to a strategy employing highly reactive urethane-protected guanidinylation reagents, particularly due to the unexpected instability of fully protected N-alkyl-N-hydroxyguanidines. The protecting-group-free method has been used for the synthesis of other N-alkyl-N-hydroxy­guanidine derivatives, namely the antibiotic N 5-hydroxy-l-arginine. These synthetic results will enable the elucidation of the properties and biological significance of the N-alkyl-N-hydroxyguanidine functionality.

Key words

natural products - antibiotics - guanidines - guanidinylation - protecting groups