title: Methylated polyamines as research tools.
abstract: 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.
authors.affiliation: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow 119991, Russia. alexkhom@list.ru
authors.forename: Alex R
authors.initials: AR
authors.lastname: Khomutov
authors.forename: Janne
authors.initials: J
authors.lastname: Weisell
authors.forename: Maxim A
authors.initials: MA
authors.lastname: Khomutov
authors.forename: Nikolay A
authors.initials: NA
authors.lastname: Grigorenko
authors.forename: Alina R
authors.initials: AR
authors.lastname: Simonian
authors.forename: Merja R
authors.initials: MR
authors.lastname: Häkkinen
authors.forename: Tuomo A
authors.initials: TA
authors.lastname: Keinänen
authors.forename: Mervi T
authors.initials: MT
authors.lastname: Hyvönen
authors.forename: Leena
authors.initials: L
authors.lastname: Alhonen
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Kochetkov
authors.forename: Jouko
authors.initials: J
authors.lastname: Vepsäläinen
mesh_terms: D020001:1-Butanol / Q000138:chemical synthesis; D001671:Biochemistry / Q000379:methods*; D008745:Methylation; D009570:Nitriles / Q000138:chemical synthesis; D013095:Spermidine / Q000737:chemistry / Q000378:metabolism*
chemical_list: D009570:Nitriles; D020001:1-Butanol; D013095:Spermidine