Russian Journal of Bioorganic Chemistry, Vol. 31, No. 2, 2005, . 183

New Syntheses of -Methyl- and , '-Dimethylspermine

N. A. Grigorenko*, J. Vepsalainen**, A. Jarvinen***, T. A. Keinanen***, L. Alhonen***, J. Janne***, and A. R. Khomutov* 1

* Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul.Vavilova 32, Moscow, 119991 Russia, ** Department of Chemistry, University of Kuopio, P. O. Box 1627 Kuopio, FIN-70211 Finland, *** Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, Kuopio, FIN-70211 Finland

Abstract: -Methylspermine and ,'-dimethylspermine were synthesized in high overall yields starting from N-(benzyloxycarbonyl)-3-aminobutanol in order to study polyamine biochemistry in vitro and in vivo.

Key words: , '-dimethylspermine, -methylspermine, polyamines, spermine/spermidine N 1 -acetyltransferase

Russian Journal of Bioorganic Chemistry, Vol. 31, No. 2, 2005, . 189

New Oxaanalogues of Spermine

A. R. Khomutov*, 1 A. R. Simonyan*, J. Vepsalainen**, T. A. Keinanen***, L. Alhonen***, and J. Janne***

* Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul Vavilova 32, Moscow, 119991 Russia, ** Department of Chemistry, University of Kuopio, P.O. Box 1627, Kuopio, FIN-70211 Finland, *** Virtanen Institute for Molecular Sciences, University of Kuopio, P.O. Box 1627, Kuopio, FIN-70211 Finland

Abstract: A new isosteric charge-deficient spermine analogue, 1,12-diamino-4,9-diaza-5-oxadodecan, and O(7-amino-4-azaheptyl)oxime of 3-aminopropanal, a stable analogue of the Schiff base intermediate in the enzymatic oxidation of spermine, were synthesized. The possible use of these compounds for the inhibition of spermine oxidase is discussed.

Key words: oxaspermine, polyamine analogues, polyamines, spermine oxidase

Russian Journal of Bioorganic Chemistry, Vol. 31, No. 3, 2005, . 271

A Charge-Deficient Analogue of Spermine with Chelating Properties

A. R. Khomutov*, 1 N. A. Grigorenko*, S. G. Skuridin*, A. V. Demin**, J. Vepsalainen***, R. A. Casero****, and P. M. Woster*****

* Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991 Russia; ** Institute of Gene Biology, Russian Academy of Sciences, ul. Vavilova 34/5, Moscow, 117984 Russia, *** Department of Chemistry, University of Kuopio, P.O. Box 1627, Kuopio, FIN-70211 Finland, **** The Sidney Kimmel Comprehensive Cancer Center, The Johns Hopkins School of Medicine, Baltimore, MD, USA, ***** Department of Pharmaceutical Sciences, Wayne State University, Detroit, MI, USA

Abstract: 1,12-Diamino-3,6,9-triazadodecane, a new isosteric and charge-deficient analogue of spermine, is synthesized. Unlike spermine, the new analogue is an excellent chelator of Cu2+ ions. Possible applications of this compound for studying enzymes of polyamine metabolism and cellular functions of spermine are discussed.

Key words: DNA, polyamines, spermine

Russian Journal of Bioorganic Chemistry ,

Vol. 31, No. 6, 2005, . 583

New Charge-Deficient Agmatine Analogues

A. R. Simonyan*, N. A. Grigorenko*, J. Vepsalainen**, and A. R. Khomutov* , 1

* Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow , 119991 Russia , ** Department of Chemistry, University of Kuopio , P.O.Box 1627 , FIN-70211, Kuopio , Finland

Abstract: N,N'-Di-Boc-N''-triflylguanidine was demonstrated to be an efficient guanidinylation reagent for O-substituted hydroxylamines. N-(3-Aminooxypropyl)- and N-(3-aminopropoxy)guanidines, previously unknown isosteric and charge-deficient agmatine analogues, have been synthesized. The possibilities of using these compounds in studying polyamine metabolism are discussed.

Key words: agmatine, polyamines, O-substituted hydroxylamines