Abstract
We report herein the synthesis and characterization of 9-(2-diallylaminoethyl) adenine. We evaluated two different synthetic routes starting with adenine where the optimal route was achieved through coupling of 9-(2-chloroethyl)adenine with diallylamine. The cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine hydrochloride salt resulted in low molecular weight oligomers in low yields. In contrast, 9-(2-diallylaminoethyl)adenine failed to cyclopolymerize, however, it formed a copolymer with SO2 in relatively good yields. The molecular weights of the cyclopolymers were around 1,700–6,000 g/mol, as estimated by SEC. The cyclo-copolymer was stable up to 226 °C. To the best of our knowledge, this is the first example of a free-radical cyclo-copolymerization of a neutral alkyldiallylamine derivative with SO2. These polymers represent a novel class of carbocyclic polynucleotides.
Highlights
Novel methods for the preparation of modified oligodeoxynucleotides (ODNs) have been actively pursued in the last two decades [1,2,3] due to their potential use in therapeutic and diagnostic applications [4]
The cyclopolymerizations of diallyl quaternary ammonium salts have been thoroughly investigated during recent years [7,8]
Adenine was protected with isobutyric anhydride and coupled to bromoethanol via the Mitsunobu reaction with triphenylphosphine (Ph3P)
Summary
Novel methods for the preparation of modified oligodeoxynucleotides (ODNs) have been actively pursued in the last two decades [1,2,3] due to their potential use in therapeutic and diagnostic applications [4]. Molecules 2012, 17 nucleases that result in the cleavage of the phosphodiester backbone in RNA and DNA [5,6]. Extensive work has been conducted to modify or replace the phosphodiester backbone, furanose ring, nucleic base or a combination of two or more. A convenient route to form homopolymers resembling modified ODNs is through the cyclopolymerization of diallylamine derivatives replacing the phosphodiester and ribose moieties simultaneously. The main interest in this research is the potential utility of the resulting polymers in industrial and pharmaceutical applications [9]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
