Methylated Polyamines as Research Tools
Earlier unknown racemic β-methylspermidine (β-MeSpd) and γ-methylspermidine (γ-MeSpd) were synthesized starting from crotononitrile or methacrylonitrile and putrescine. Lithium aluminum hydride reduction of the intermediate di-Boc-nitriles resulted in corresponding di-Boc-amines, which after deprotection gave target β- and γ-MeSpd’s. To prepare α-MeSpd, the starting compound, 3-amino-1-butanol, was converted into N-Cbz-3-amino-1-butyl methanesulfonate, which alkylated putrescine to give (after deprotection of amino group) the required α-MeSpd. Novel β- and γ-MeSpd’s in combination with earlier α-MeSpd are useful tools for studying enzymology and cell biology of polyamines.
Key wordsPolyamines C-methylated spermidine analogs
This work was supported by the Academy of Finland (project nos. 124185 and 128702), the Russian Foundation for Basic Research (project nos. 09-04-01272, and 08-04-91777), and the program Molecular and Cell Biology of the Presidium of the Russian Academy of Sciences.
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