DC Field | Value | Language |
dc.contributor.author | ROSEMEYER, H | |
dc.contributor.author | SEELA, F | |
dc.date.accessioned | 2021-12-23T16:03:25Z | - |
dc.date.available | 2021-12-23T16:03:25Z | - |
dc.date.issued | 1991 | |
dc.identifier.issn | 0018019X | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/5978 | - |
dc.description.abstract | 1-(2'-Deoxy-beta-D-threo-pentofuranosyl)thymine (= 1-(2'-deoxy-beta-D-xylofuranosyl)thymine; xT(d); 2) was converted into its phosphonate 3b as well as its 2-cyanoethyl phosphoramidite 3c. Both compounds were used for solid-phase synthesis of d[(xT)12-T] (5), representing the first DNA fragment build up from 3'-5'-linked 2'-deoxy-beta-D-xylonucleosides. Moreover, xT(d) was introduced into the innermost part of the self-complementary dodecamer d(G-T-A-G-A-A-xT-xT-C-T-A-C)2 (9). The CD spectrum of d[(xT)12-T] (5) exhibits reversed Cotton effects compared to d(T12) (6; see Fig. 1), implying a left-handed single strand. With d(A12) (7) it could be hybridized to form a propably left-handed double strand d(A12).d[(xT)12-T] (7.5) which was confirmed by melting experiments in combination with temperature-dependent CD spectroscopy. While 5 was hydrolyzed by snake-venom phosphodiesterase, it was resistant towards calf-spleen phosphodiesterase. The modified, self-complementary duplex 9 was hydrolyzed completely by snake-venom phosphodiesterase, at a twelvefold slower rate compared to unmodified 8; calf-spleen phosphodiesterase hydrolyzed 9 only partially. | |
dc.language.iso | en | |
dc.publisher | NEW SWISS CHEMICAL SOC | |
dc.relation.ispartof | HELVETICA CHIMICA ACTA | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | CONFORMATIONAL-ANALYSIS | |
dc.subject | DEOXYADENOSINE | |
dc.subject | NUCLEOSIDES | |
dc.subject | NUCLEOTIDES | |
dc.subject | SUGAR RING | |
dc.title | 1-(2'-DEOXY-BETA-D-XYLOFURANOSYL)THYMINE BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND PROPERTIES OF OLIGO(2'-DEOXYXYLONUCLEOTIDES) | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/hlca.19910740408 | |
dc.identifier.isi | ISI:A1991FU74800007 | |
dc.description.volume | 74 | |
dc.description.issue | 4 | |
dc.description.startpage | 748 | |
dc.description.endpage | 760 | |
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 | - |