1-(2'-DEOXY-BETA-D-XYLOFURANOSYL)CYTOSINE - BASE-PAIRING OF OLIGONUCLEOTIDES WITH A CONFIGURATIONALLY ALTERED SUGAR-PHOSPHATE BACKBONE
DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | SEELA, F | |
dc.contributor.author | WORNER, K | |
dc.contributor.author | ROSEMEYER, H | |
dc.date.accessioned | 2021-12-23T16:04:33Z | - |
dc.date.available | 2021-12-23T16:04:33Z | - |
dc.date.issued | 1994 | |
dc.identifier.issn | 0018019X | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/6483 | - |
dc.description.abstract | Solid-phase synthesis of the oligo(2'-deoxynucleotides) 19 and 20 containing 2'-deoxy-beta-D-xylocytidine (4) is described. For this purpose, 1-(2-deoxy-beta-D-threo-pentofuranosyl)cytosine (= 1-(2-deoxy-beta-D-xyiofuranosyl)cytosine; 4) was protected at its 4-NH2 group with a benzoyl (-->5) or an isobutyryl (-->8) residue, and a dimethoxytrityl group was introduced at 5'-OH (-->7, 10; Scheme 2). Compounds 7 and 10 were converted into the 3'-phosphonates 11a,b. While 19 could be hybridized with 21 and 22 under formation of duplexes with a two-nucleotide overhang on both termini (19.21: T-m 29 degrees;19.22:T-m 22 degrees), the decamer 20 bearing four C-x(d) residues could no longer be hybridized with one of the opposite strands. Moreover, the oligonucleotides d[(xC)(8)-C] (13), d[(xC)(4)-C] (14), d[C-(xC)(4)-C] (15), and d[C-(xC)(3)-C] (16) were synthesized. While 13 exhibits an almost inverted CD spectrum compared to d(C-9) (17), the other oligonucleotides show CD spectra typical for regular right-handed single helices. At pH 5, d[(xC)(8)-C] forms a stable hemi-protonated duplex which exhibits a T-m of 60 degrees (d[(CH+)(9)].d(C-9): T-m 36 degrees). The thermodynamic parameters of duplex formation of (13H(+).13) and (17H(+).17) were calculated from their melting profiles and were found to be identical in Delta H but differ in Delta S (13H(+).13:Delta S = -287 cal/K mol; 17H(+).17: Delta S = -172 cal/K mol). | |
dc.language.iso | en | |
dc.publisher | NEW SWISS CHEMICAL SOC | |
dc.relation.ispartof | HELVETICA CHIMICA ACTA | |
dc.subject | BUILDING-BLOCKS | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | CONFORMATIONAL-ANALYSIS | |
dc.subject | DNA | |
dc.subject | NUCLEOSIDES | |
dc.subject | SOLID-PHASE SYNTHESIS | |
dc.subject | STRANDS | |
dc.title | 1-(2'-DEOXY-BETA-D-XYLOFURANOSYL)CYTOSINE - BASE-PAIRING OF OLIGONUCLEOTIDES WITH A CONFIGURATIONALLY ALTERED SUGAR-PHOSPHATE BACKBONE | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/hlca.19940770402 | |
dc.identifier.isi | ISI:A1994NV50400001 | |
dc.description.volume | 77 | |
dc.description.issue | 4 | |
dc.description.startpage | 883 | |
dc.description.endpage | 896 | |
dc.publisher.place | VERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND | |
dcterms.isPartOf.abbreviation | Helv. Chim. Acta | |
crisitem.author.dept | Institut für Chemie neuer Materialien | - |
crisitem.author.deptid | institute11 | - |
crisitem.author.parentorg | FB 05 - Biologie/Chemie | - |
crisitem.author.grandparentorg | Universität Osnabrück | - |
crisitem.author.netid | RoHe783 | - |
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geprüft am 30.04.2024