Literature DB >> 21318892

Methylated polyamines as research tools.

Alex R Khomutov1, Janne Weisell, Maxim A Khomutov, Nikolay A Grigorenko, Alina R Simonian, Merja R Häkkinen, Tuomo A Keinänen, Mervi T Hyvönen, Leena Alhonen, Sergey N Kochetkov, Jouko Vepsäläinen.   

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.

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Year:  2011        PMID: 21318892     DOI: 10.1007/978-1-61779-034-8_29

Source DB:  PubMed          Journal:  Methods Mol Biol        ISSN: 1064-3745


  3 in total

1.  Effects of novel C-methylated spermidine analogs on cell growth via hypusination of eukaryotic translation initiation factor 5A.

Authors:  Mervi T Hyvönen; Tuomo A Keinänen; Maxim Khomutov; Alina Simonian; Jouko Vepsäläinen; Jong Hwan Park; Alex R Khomutov; Leena Alhonen; Myung Hee Park
Journal:  Amino Acids       Date:  2011-08-23       Impact factor: 3.520

2.  The Essential Role of Spermidine in Growth of Agrobacterium tumefaciens Is Determined by the 1,3-Diaminopropane Moiety.

Authors:  Sok Ho Kim; Yi Wang; Maxim Khomutov; Alexey Khomutov; Clay Fuqua; Anthony J Michael
Journal:  ACS Chem Biol       Date:  2015-12-28       Impact factor: 5.100

3.  Unforeseen Possibilities To Investigate the Regulation of Polyamine Metabolism Revealed by Novel C-Methylated Spermine Derivatives.

Authors:  Maxim Khomutov; Mervi T Hyvönen; Alina Simonian; Andrey A Formanovsky; Irina V Mikhura; Alexander O Chizhov; Sergey N Kochetkov; Leena Alhonen; Jouko Vepsäläinen; Tuomo A Keinänen; Alex R Khomutov
Journal:  J Med Chem       Date:  2019-12-13       Impact factor: 7.446

  3 in total

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