Synthesis of optically active polynucleotide analogs with poly(vinyl alcohol)s as backbones and adenine and 5-bromouracil derivatives as pendants
dc.contributor.author | Overberger, Charles Gilbert | en_US |
dc.contributor.author | Chang, Ji Young | en_US |
dc.date.accessioned | 2006-04-28T18:18:54Z | |
dc.date.available | 2006-04-28T18:18:54Z | |
dc.date.issued | 1989-10 | en_US |
dc.identifier.citation | Overberger, C. G.; Chang, Ji Young (1989)."Synthesis of optically active polynucleotide analogs with poly(vinyl alcohol)s as backbones and adenine and 5-bromouracil derivatives as pendants." Journal of Polymer Science Part A: Polymer Chemistry 27(11): 3589-3602. <http://hdl.handle.net/2027.42/38835> | en_US |
dc.identifier.issn | 0887-624X | en_US |
dc.identifier.issn | 1099-0518 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/38835 | |
dc.description.abstract | The optically active polynucleotide analogs were prepared by grafting nucleic acid base derivatives onto poly(vinyl alcohol). The ( R )-ethyl 2-(5-bromouracil-1-yl)propanoate was obtained either by reaction of 5-bromouracil sodium salt with ( S )-ethyl 2-[(methylsulfonyl)oxy]propanoate or reaction of 5-bromouracil with ( S )-ethyl lactate in the presence of triphenyl phosphine and diethyl azodicarboxylate. Subsequent hydrolysis of the ester is aqueous acid provided the optically pure ( R )-bromouracilypropanoic acid. The monomer model compounds were prepared by an esterification reaction of the pendant groups with 3-pentyl alcohol in the presence of dicyclohexylcarbodiimide and a catalytic amount of 4-pyrrolidinopyridine. Poly(vinyl alcohol) underwent reaction with the ( R )-bromouracilylpropanoic acid or the ( R )-adeninylpropanoic acid in the presence of dicyclohexylcarbodiimide and a catalytic amount of 4-pyrrolidinopyridine. The resulting polymers were optically active and percents grafting were almost quantitative. | en_US |
dc.format.extent | 744286 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | John Wiley & Sons, Inc. | en_US |
dc.subject.other | Chemistry | en_US |
dc.subject.other | Polymer and Materials Science | en_US |
dc.title | Synthesis of optically active polynucleotide analogs with poly(vinyl alcohol)s as backbones and adenine and 5-bromouracil derivatives as pendants | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Chemistry and the Macromolecular Research Center, The University of Michigan, Ann Arbor, Michigan 48109 | en_US |
dc.contributor.affiliationum | Department of Chemistry and the Macromolecular Research Center, The University of Michigan, Ann Arbor, Michigan 48109 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/38835/1/080271104_ftp.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1002/pola.1989.080271104 | en_US |
dc.identifier.source | Journal of Polymer Science Part A: Polymer Chemistry | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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