Aminooxy Analogues of Spermine and their Monoacetyl Derivatives

A. R. Simonyan1, J. Vepsalainen2, and A. R. Khomutov1 #

#Phone: (495) 135-60-65; fax: (495) 135-14-05; e-mail:
1Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991, Russia
2Department of Chemistry, University of Kuopio, P.O. Box 1627, FIN-70211 Kuopio, Finland

Received: April 7, 2006;  in final form: April 20, 2006

Abstract: Convenient methods of synthesis of 1-aminooxy-3,8-diaza-11-aminoundecane, its earlier unknown N 1- and N 11-acetyl derivatives, and also 1,10-bis(aminooxy)-3,8-diazadecane are suggested. It is shown that it is possible to selectively delete the acid-labile ethoxyethylidene protection of aminooxy group by hydrosulfates in the presence of N-tert-butyloxycarbonyl group.

Key words: N 1-acetylspermine, polyamine analogues, spermine, O-substituted hydroxylamine

Russian Journal of Bioorganic Chemistry 2006, 32 (6): 578-585