Matches in SemOpenAlex for { <https://semopenalex.org/work/W1987648764> ?p ?o ?g. }
Showing items 1 to 88 of
88
with 100 items per page.
- W1987648764 endingPage "1330" @default.
- W1987648764 startingPage "1311" @default.
- W1987648764 abstract "A new type of oligonucleosides has been devised to investigate the potential of oligonucleosides with a nucleobase-including backbone to form homo- and/or heteroduplexes (cf. Fig. 2). It is characterised by ethynyl-linkages between C(5′) and C(6) of uridine, and between C(5′) and C(8) of adenosine. Force-field calculations and Maruzen model studies suggest that such oligonucleosides form autonomous pairing systems and hybridize with RNA. We describe the syntheses of uridine-derived monomers, suitable for the construction of oligomers, and of a dimer. Treatment of uridine-5′-carbaldehyde (2) with triethylsilyl acetylide gave the diastereoisomeric propargylic alcohols 6 and 7 (1 : 2, 80%; Scheme 1). Their configuration at C(5′) was determined on the basis of NOE experiments and X-ray crystal-structure analysis. Iodination at C(6) of the (R)-configured alcohol 7 by treatment with lithium diisopropylamide (LDA) and N-iodosuccinimide (NIS) gave the iodide 17 (62%), which was silylated at O−C(5′) to yield 18 (89%; Scheme 2). C-Desilylation of 7 with NaOH in MeOH/H2O led to the alkyne 10 (98%); O-silylation of 10 at O−C(5′) gave 16 (84%). Cross-coupling of 18 and 16 yielded 63% of the dimer 19, which was C-desilylated to 20 in 63% yield. Cross-coupling of 10 and the 6-iodouridine 13 (70%), followed by treatment of the resulting dimer 14 with HF and HCl in MeCN/H2O, gave the deprotected dimer 15 (73%)." @default.
- W1987648764 created "2016-06-24" @default.
- W1987648764 creator A5041165489 @default.
- W1987648764 creator A5047123097 @default.
- W1987648764 creator A5070811586 @default.
- W1987648764 creator A5075695962 @default.
- W1987648764 date "2000-07-05" @default.
- W1987648764 modified "2023-10-16" @default.
- W1987648764 title "Oligonucleosides with a Nucleobase-Including Backbone, Part 1, Concept, Force-Field Calculations, and Synthesis of Uridine-Derived Monomers and Dimers" @default.
- W1987648764 doi "https://doi.org/10.1002/1522-2675(20000705)83:7<1311::aid-hlca1311>3.0.co;2-2" @default.
- W1987648764 hasPublicationYear "2000" @default.
- W1987648764 type Work @default.
- W1987648764 sameAs 1987648764 @default.
- W1987648764 citedByCount "27" @default.
- W1987648764 countsByYear W19876487642013 @default.
- W1987648764 countsByYear W19876487642014 @default.
- W1987648764 countsByYear W19876487642015 @default.
- W1987648764 countsByYear W19876487642017 @default.
- W1987648764 countsByYear W19876487642020 @default.
- W1987648764 countsByYear W19876487642022 @default.
- W1987648764 crossrefType "journal-article" @default.
- W1987648764 hasAuthorship W1987648764A5041165489 @default.
- W1987648764 hasAuthorship W1987648764A5047123097 @default.
- W1987648764 hasAuthorship W1987648764A5070811586 @default.
- W1987648764 hasAuthorship W1987648764A5075695962 @default.
- W1987648764 hasConcept C104317684 @default.
- W1987648764 hasConcept C118629725 @default.
- W1987648764 hasConcept C134121241 @default.
- W1987648764 hasConcept C145148216 @default.
- W1987648764 hasConcept C166940927 @default.
- W1987648764 hasConcept C178790620 @default.
- W1987648764 hasConcept C185592680 @default.
- W1987648764 hasConcept C191897082 @default.
- W1987648764 hasConcept C192562407 @default.
- W1987648764 hasConcept C2779072608 @default.
- W1987648764 hasConcept C2779546866 @default.
- W1987648764 hasConcept C2779627003 @default.
- W1987648764 hasConcept C2781259782 @default.
- W1987648764 hasConcept C521977710 @default.
- W1987648764 hasConcept C552990157 @default.
- W1987648764 hasConcept C55493867 @default.
- W1987648764 hasConcept C61234307 @default.
- W1987648764 hasConcept C65973085 @default.
- W1987648764 hasConcept C67705224 @default.
- W1987648764 hasConcept C71240020 @default.
- W1987648764 hasConcept C8010536 @default.
- W1987648764 hasConceptScore W1987648764C104317684 @default.
- W1987648764 hasConceptScore W1987648764C118629725 @default.
- W1987648764 hasConceptScore W1987648764C134121241 @default.
- W1987648764 hasConceptScore W1987648764C145148216 @default.
- W1987648764 hasConceptScore W1987648764C166940927 @default.
- W1987648764 hasConceptScore W1987648764C178790620 @default.
- W1987648764 hasConceptScore W1987648764C185592680 @default.
- W1987648764 hasConceptScore W1987648764C191897082 @default.
- W1987648764 hasConceptScore W1987648764C192562407 @default.
- W1987648764 hasConceptScore W1987648764C2779072608 @default.
- W1987648764 hasConceptScore W1987648764C2779546866 @default.
- W1987648764 hasConceptScore W1987648764C2779627003 @default.
- W1987648764 hasConceptScore W1987648764C2781259782 @default.
- W1987648764 hasConceptScore W1987648764C521977710 @default.
- W1987648764 hasConceptScore W1987648764C552990157 @default.
- W1987648764 hasConceptScore W1987648764C55493867 @default.
- W1987648764 hasConceptScore W1987648764C61234307 @default.
- W1987648764 hasConceptScore W1987648764C65973085 @default.
- W1987648764 hasConceptScore W1987648764C67705224 @default.
- W1987648764 hasConceptScore W1987648764C71240020 @default.
- W1987648764 hasConceptScore W1987648764C8010536 @default.
- W1987648764 hasIssue "7" @default.
- W1987648764 hasLocation W19876487641 @default.
- W1987648764 hasOpenAccess W1987648764 @default.
- W1987648764 hasPrimaryLocation W19876487641 @default.
- W1987648764 hasRelatedWork W1982943841 @default.
- W1987648764 hasRelatedWork W2003560954 @default.
- W1987648764 hasRelatedWork W2021817055 @default.
- W1987648764 hasRelatedWork W2054084566 @default.
- W1987648764 hasRelatedWork W2057619835 @default.
- W1987648764 hasRelatedWork W2079171507 @default.
- W1987648764 hasRelatedWork W2144956714 @default.
- W1987648764 hasRelatedWork W2515999156 @default.
- W1987648764 hasRelatedWork W2952792681 @default.
- W1987648764 hasRelatedWork W2953092038 @default.
- W1987648764 hasVolume "83" @default.
- W1987648764 isParatext "false" @default.
- W1987648764 isRetracted "false" @default.
- W1987648764 magId "1987648764" @default.
- W1987648764 workType "article" @default.