Synthesis and Stability of GNRA-Loop Analogs

Nebularine, 9‐(β‐D‐ribofuranosyl)‐9H‐purin‐2‐amine, and inosine phosphoramidites 8, 16, and 17, respectively, were synthesized and incorporated into the GNRA tetraloop at different positions (see Scheme, Table, and Fig. 4). The oligomers were investigated by means of UV and CD spectroscopy to addres...

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Veröffentlicht in:Helvetica chimica acta Jg. 82; H. 12; S. 2094 - 2104
Hauptverfasser: Wörner, Karlheinz, Strube, Thorsten, Engels, Joachim W.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Basel Verlag Helvetica Chimica Acta 15.12.1999
Wiley
Schlagworte:
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
RNA-SYNTHESIS
HAIRPINS
TETRALOOPS
STRUCTURAL FEATURES
SEQUENCE
DEPENDENCE
ISSN:0018-019X, 1522-2675
Online-Zugang:Volltext
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Zusammenfassung:Nebularine, 9‐(β‐D‐ribofuranosyl)‐9H‐purin‐2‐amine, and inosine phosphoramidites 8, 16, and 17, respectively, were synthesized and incorporated into the GNRA tetraloop at different positions (see Scheme, Table, and Fig. 4). The oligomers were investigated by means of UV and CD spectroscopy to address the question of how the individual base‐modified N‐nucleosides contribute to changes in H‐bonding and base‐stacking interactions within the loop. Several CD spectra are given and compared with each other (Figs. 5 and 6). The exchange of the loop sequence in position 4 and 7 results in a distinct change in base stacking. CD‐Band shifting allows us to advance the hypothesis that a transition from a GNRA‐type towards a UNCG‐type base stacking is observed.
Bibliographie:ark:/67375/WNG-K21VCMGV-K
ArticleID:HLCA2094
istex:3607157C8E4309FC6F5F1F3F4AB66424611B73A2
ISSN:0018-019X
1522-2675
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2094::AID-HLCA2094>3.0.CO;2-H