784213-60-1Relevant articles and documents
α-methyl polyamines: Efficient synthesis and tolerance studies in vivo and in vitro. First evidence for dormant stereospecificity of polyamine oxidase
J?rvinen, Aki J.,Cerrada-Gimenez, Marc,Grigorenko, Nikolay A.,Khomutov, Alex R.,Veps?l?inen, Jouko J.,Sinervirta, Riitta M.,Kein?nen, Tuomo A.,Alhonen, Leena I.,J?nne, Juhani E.
, p. 399 - 406 (2007/10/03)
Efficient syntheses of metabolically stable α-methylspermidine 1, α-methylspermine 2, and bis-α,α-methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N1- acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.
