Synthesis of polynucleotide analogs by grafting optically active adenine, cytosine, and hypoxanthine derivatives onto polytrimethylenimine
dc.contributor.author | Overberger, Charles Gilbert | en_US |
dc.contributor.author | Chang, Ji Young | en_US |
dc.date.accessioned | 2006-04-28T18:18:57Z | |
dc.date.available | 2006-04-28T18:18:57Z | |
dc.date.issued | 1989-11 | en_US |
dc.identifier.citation | Overberger, C. G.; Chang, Ji Young (1989)."Synthesis of polynucleotide analogs by grafting optically active adenine, cytosine, and hypoxanthine derivatives onto polytrimethylenimine." Journal of Polymer Science Part A: Polymer Chemistry 27(12): 4013-4033. <http://hdl.handle.net/2027.42/38836> | en_US |
dc.identifier.issn | 0887-624X | en_US |
dc.identifier.issn | 1099-0518 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/38836 | |
dc.description.abstract | A new family of polynucleotide analogs were prepared by grafting nucleic acid base derivatives onto polytrimethylenimine. Several new optically pure Α-nucleic acid base substituted propanoic acids were prepared as pendant groups. The ( R )-ethyl adeninylpropanoate was obtained from adenine and ( S )-ethyl lactate by utilizing a diethyl azodicarboxylate-triphenyl phosphine method. Subsequent hydrolysis of the ester in aqueous acid gave the ( R )-adeninylpropanoic acid without racemization. The reaction of cytosine sodium salt with ( S )-ethyl 2-[(methylsulfonyl)oxy] propanoate produced the 20% racemized ( R )-ethyl 2-(cytosin-1-yl)propanoate. The optically pure ester was obtained by recrystallization from ethyl alcohol, which was hydrolyzed in aqueous acid to give the ( R )-acid with 66% enantiomeric excess. The ( R )-2-(hypoxanthin-9-yl)propanoic acid was prepared by reaction of ( R )-2-(adenin-9-yl)propanoic acid with sodium nitrite. The pendant groups were allowed to react with N -hydroxy compounds in the presence of dicyclohexylcarbodiimide to give the active esters. These active esters underwent reaction with N , N -dipropylamine to provide monomer model compounds. The pendant groups were grafted onto polytrimethylenimine by using the active ester method. The racemization reactions were observed in the grafting reactions. The resulting polymers showed a range of percent grafting from 60 to 80%. | en_US |
dc.format.extent | 1189286 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 polynucleotide analogs by grafting optically active adenine, cytosine, and hypoxanthine derivatives onto polytrimethylenimine | 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/2027.42/38836/1/080271212_ftp.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1002/pola.1989.080271212 | 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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