Unrecognized Cycloaddition Reactions of N-Alkyl-α,β-Unsaturated Imines Occurring in Biosystems and Their Biological Roles

Despite being fundamentally ubiquitous and important species in organic and bioorganic chemistry, the reactivities of N -alkyl-α,β-unsaturated imines have not been thoroughly explored due to their instability. Here, we describe novel reactivities of N -alkyl-α,β-unsaturated imines, which derived fro...

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Bibliographic Details
Published in:BioNanoScience 2016-12, Vol.6 (4), p.364-367
Main Authors: Pradipta, Ambara R., Tsutsui, Ayumi, Latypova, Liliya, Chulakova, Dilyara, Smirnov, Ivan, Kurbangalieva, Almira, Tanaka, Katsunori
Format: Article
Language:English
Subjects:
Acrolein
Alcohols
Aldehydes
Alkylamines
Amines
Amyloid
Biogenic amines
Biological and Medical Physics
Biomaterials
Biophysics
Circuits and Systems
Cycloaddition
Diamines
Engineering
Fibrillogenesis
Formaldehyde
Imines
Nanotechnology
Noradrenaline
Norepinephrine
Oxidative stress
Polyamines
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Summary:Despite being fundamentally ubiquitous and important species in organic and bioorganic chemistry, the reactivities of N -alkyl-α,β-unsaturated imines have not been thoroughly explored due to their instability. Here, we describe novel reactivities of N -alkyl-α,β-unsaturated imines, which derived from α,β-unsaturated aldehydes (e.g., unsubstituted or substituted acrolein), alkylamines (e.g., amino-alcohols or diamines), and formaldehyde to produce 1,5-diazacyclooctanes, hexahydropyrimidines, and 1,3,5-triazacyclooctanes via formal [4 + 4], [4 + 2], and [4 + 2 + 2] cycloadditions in a stereocontrolled manner. We then also synthetically demonstrated that reaction between acrolein and biogenic amines (e.g., polyamines, noradrenaline, sphingosine), which ubiquitously exist in biosystems, proceed smoothly to give the corresponding 1,5-diazacyclooctanes. Finally, we also examined biological functions of the cycloaddition products and revealed for the first time their roles in oxidative stress mechanism and inhibition of amyloid-β (Aβ) 1-40 fibrillization.
ISSN:2191-1630
2191-1649
DOI:10.1007/s12668-016-0236-7