DC Field | Value | Language |
dc.contributor.author | Jana, Sunit K. | |
dc.contributor.author | Leonard, Peter | |
dc.contributor.author | Ingale, Sachin A. | |
dc.contributor.author | Seela, Frank | |
dc.date.accessioned | 2021-12-23T16:05:36Z | - |
dc.date.available | 2021-12-23T16:05:36Z | - |
dc.date.issued | 2016 | |
dc.identifier.issn | 14770520 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7099 | - |
dc.description.abstract | Oligonucleotides containing 2'-O-methylated 5-methylisocytidine (3) and 2'-O-propargyl-5-methylisocytidine (4) as well as the non-functionalized 5-methyl-2'-deoxyisocytidine (1b) were synthesized. MALDI-TOF mass spectra of oligonucleotides containing 1b are susceptible to a stepwise depyrimidination. In contrast, oligonucleotides incorporating 2'-O-alkylated nucleosides 3 and 4 are stable. This is supported by acid catalyzed hydrolysis experiments performed on nucleosides in solution. 2'-O-Alkylated nucleoside 3 was synthesized from 2'-O-5-dimethyluridine via tosylation, anhydro nucleoside formation and ring opening. The corresponding 4 was obtained by direct regioselective alkylation of 5-methylisocytidine (1d) with propargyl bromide under phase-transfer conditions. Both compounds were converted to phosphoramidites and employed in solid-phase oligonucleotide synthesis. Hybridization experiments resulted in duplexes with antiparallel or parallel chains. In parallel duplexes, methylation or propargylation of the 2'-hydroxyl group of isocytidine leads to destabilization while in antiparallel DNA this effect is less pronounced. 2'-O-Propargylated 4 was used to cross-link nucleosides and oligonucleotides to homodimers by a stepwise click ligation with a bifunctional azide. | |
dc.description.sponsorship | ChemBiotech, Munster, Germany; We would like to thank Dr S. Budow-Busse for helpful discussions and support while preparing the manuscript. We appreciate Dr Yang He for providing us with the oligonucleotide used in the mass degradation experiment. We also thank Dr H. Mei for recording the NMR spectra and Dr M. Letzel, Organisch-Chemisches Institut, Universitat Munster, Germany, for the recording of the MALDI spectra. Financial support by ChemBiotech, Munster, Germany, is highly appreciated. | |
dc.language.iso | en | |
dc.publisher | ROYAL SOC CHEMISTRY | |
dc.relation.ispartof | ORGANIC & BIOMOLECULAR CHEMISTRY | |
dc.subject | CATALYZED HYDROLYSIS | |
dc.subject | CHAIN ORIENTATION | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | CLICK CHEMISTRY | |
dc.subject | DNA DUPLEX | |
dc.subject | DOUBLE HELIX | |
dc.subject | ENZYMATIC INCORPORATION | |
dc.subject | MASS-SPECTROMETRY | |
dc.subject | OLIGONUCLEOTIDE DUPLEXES | |
dc.subject | RESIDUES SYNTHESIS | |
dc.subject | TERMINAL ALKYNES | |
dc.title | 2 `-O-Methyl- and 2 `-O-propargyl-5-methylisocytidine: synthesis, properties and impact on the isoC(d)-dG and the isoC(d)-isoG(d) base pairing in nucleic acids with parallel and antiparallel strand orientation | |
dc.type | journal article | |
dc.identifier.doi | 10.1039/c6ob00622a | |
dc.identifier.isi | ISI:000378103100020 | |
dc.description.volume | 14 | |
dc.description.issue | 21 | |
dc.description.startpage | 4927 | |
dc.description.endpage | 4942 | |
dc.identifier.eissn | 14770539 | |
dc.publisher.place | THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND | |
dcterms.isPartOf.abbreviation | Org. Biomol. Chem. | |