Synthesis of polynucleotide analogs by grafting optically active nucleic acid base derivatives onto polyethylenimine Preliminary results are reported in J. Polym. Sci. Polym. Chem. Ed. , 24 , 167 (1986).

Polynucleotide analogs with a polyethylenimine backbone and optically active thymine- and adenine-containing pendants and their model compounds were synthesized. The pendants were prepared by the addition reaction of the nucleic acid base to ethyl crotonate. The ammonium salt of 3-(adenin-9-yl)butyric acid was employed to replace its free acid for the formation of diastereomeric salt with brucine. Fractional crystallization of the diastereomeric salt generates the partially resolved enantiomers. The solubility difference between the racemic mixture and its enantiomer was utilized to obtain the pure enantiomers. The active esters of the pendants were prepared. Grafting reactions were carried out by the reaction of active esters with PEI at room temperature. Completely grafted polymers were obtained.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/38826/1/080250133_ftp.pd

Grafting of optically active nucleic acid base derivatives onto poly(vinylamine) as polynucleotide analogs Preliminary results are reported in J. Polym. Sci. Polym. Lett. Ed. , 23 , 345 (1985).

Polynucleotide analogs consisting of poly(vinylamine) as the backbone and optically active thymine and adenine derivatives as the pendants were synthesized. The pendants were prepared by the addition reaction of the nucleic acid base to ethyl crotonate followed by hydrolysis. The pendants were resolved using brucine as the resolving agent and an acetone-water mixture as the fractional crystallization solvent. The active esters of the pendants also were prepared. Poly(vinylamine) was isolated from water employing a weak acid, N -hydroxysuccinimide (HOSu), to protect the amino group of the poly(vinylamine). Model reactions for grafting were examined. Grafting reactions were carried out by reacting the active esters with the PVAm.6HOSu complex at room temperature.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/38827/1/080250134_ftp.pd

The reaction of optically active nucleic acid base derivative with polyvinylamine in nonaqueous media: Grafting reaction

No Abstract.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/38736/1/130230611_ftp.pd

Novel optical resolution of an unprotected adenine derivative followed by grafting the pendant onto polyethylenimine

No Abstract.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/38818/1/080240115_ftp.pd

Syntheses of stereoregular and optically active polyamides from active 4-chloro-1-benzotriazolyl diesters and diamines

A new route to prepare optically active polyamides was established, based on the polycondensation of two new active diesters: the active diesters of 4-chloro-1 hydroxybenzotriazole, such as 1,1'-(terephthaloyldioxy)bis(4-chloro-benzotriazole), and 1,1'-(isophthaloyldioxy)bis(4-chlorobenzotriazole), with optically active isomers of 2,4-diaminopentane. Dipolar aprotic solvents such as N , N -dimethylformamide and dimethyl sulfoxide were used as reaction solvents. The solution polycondensation carried out in solution at room temperature afforded optically active polyamides. The aminolysis of the two active diesters was carried out as a model reaction study.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/38817/1/080240106_ftp.pd