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New Charge-Deficient Agmatine Analogues

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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.

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Abbreviations

Agm:

agmatine (1-guanidino-4-aminobutane)

AO-Agm:

N-(3-aminooxypropyl)guanidine

ArgDC:

arginine decarboxylase

GAPA:

N-(3-aminopropoxy)guanidine

ODC:

ornithine decarboxylase

Put:

putrescine (1,4-diaminobutane)

Tf:

triflate (trifluoromethanesulfonate)

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Authors and Affiliations

  1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991, Russia

    A. R. Simonyan, N. A. Grigorenko & A. R. Khomutov

  2. Department of Chemistry, University of Kuopio, P.O.Box 1627, FIN-70211, Kuopio, Finland

    J. Vepsalainen

Authors
  1. A. R. Simonyan
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  2. N. A. Grigorenko
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  3. J. Vepsalainen
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  4. A. R. Khomutov
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Correspondence to A. R. Khomutov.

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__________

Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 6, 2005, pp. 645–650.

Original Russian Text Copyright © 2005 by Simonyan, Grigorenko, Vepsalainen, Khomutov.

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Simonyan, A.R., Grigorenko, N.A., Vepsalainen, J. et al. New Charge-Deficient Agmatine Analogues. Russ J Bioorg Chem 31, 583–587 (2005). https://doi.org/10.1007/s11171-005-0080-y

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  • DOI: https://doi.org/10.1007/s11171-005-0080-y

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