Oligonucleotides containing 7-propynyl-7-deazaguanine: synthesis and base pair stability
Autor(en): | Seela, F Shaikh, KI |
Stichwörter: | 7-deaza-7-propynyl-2 `-deoxyguanosine; 7-deazapurine; 8-aza-7-deazapurine; ANTISENSE GENE INHIBITION; Chemistry; Chemistry, Organic; DNA; DUPLEX STABILITY; MOLECULAR RECOGNITION; NUCLEIC-ACIDS; OLIGODEOXYNUCLEOTIDES; oligonucleotides; PROPYNE ANALOGS; RNASE-H; STRUCTURAL-PROPERTIES | Erscheinungsdatum: | 2005 | Herausgeber: | PERGAMON-ELSEVIER SCIENCE LTD | Enthalten in: | TETRAHEDRON | Band: | 61 | Ausgabe: | 10 | Startseite: | 2675 | Seitenende: | 2681 | Zusammenfassung: | Oligonucleotides incorporating the propynyl derivative of 7-deaza-2'-deoxyguanosine (1) were synthesized by solid-phase oligonucleotide synthesis. As building blocks the phosphoramidites 7a,b were prepared. The incorporation of 1 into oligonucleotides exerts a positive effect on the DNA duplex stability. The duplex stabilization by 1 was higher than that of 7-iodo-7-deaza-2-deoxyguanosine (2b). The stabilizing effect of the 7-propynyl group introduced in the 7-deazapurines is similar to that reported for 8-aza-7-deazapurines. From CD spectra it was deduced that the B-DNA structure is not significantly altered by compound 1. (C) 2005 Elsevier Ltd. All rights reserved. |
ISSN: | 00404020 | DOI: | 10.1016/j.tet.2005.01.060 |
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geprüft am 06.06.2024