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Synthesis of novel deuterium labelled derivatives of N-alkylated polyamines
Authors:Merja R Häkkinen  Tuomo A Keinänen  Seppo Auriola  Leena Alhonen  Jouko Vepsäläinen
Institution:a Department of Biosciences, Laboratory of Chemistry, Biocenter Kuopio, University of Kuopio, PO Box 1627, FI-70211 Kuopio, Finland
b Department of Biotechnology and Molecular Medicine, A.I. Virtanen Institute for Molecular Sciences, Biocenter Kuopio, University of Kuopio, PO Box 1627, FI-70211 Kuopio, Finland
c Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov Street 32, Moscow 119991, Russia
d Department of Pharmaceutical Chemistry, Biocenter Kuopio, University of Kuopio, PO Box 1627, FI-70211 Kuopio, Finland
Abstract:Novel di-, tetra- and octadeuterated derivatives of mono-N-alkylated diaminopropanes, spermidines, spermines, symmetrically bis-N-alkylated spermines and unsymmetrically bis-N-alkylated spermines were synthesized. Deuterium labels were introduced into the RHNCH2CH2CN intermediate either by exchanging the protons next to the nitrile group under basic conditions with D2O-EtOD mixture or/and by reducing the nitrile group to a CD2-NH2 fragment with LiAlD4.
Keywords:Polyamines  Deuterated polyamines  Deuterated  N-Alkylated polyamine analogues
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