Parallel Stranded DNA Stabilized with Internal Sugar Cross-Links: Synthesis and Click Ligation of Oligonucleotides Containing 2 `-Propargylated Isoguanosine

Autor(en): Pujari, Suresh S.
Seela, Frank
Stichwörter: 2'-DEOXYISOGUANOSINE; AZIDE; BASE; Chemistry; Chemistry, Organic; CONJUGATION; CRYSTAL-STRUCTURE; DUPLEX DNA; GUANINE; GUANOSINE; NUCLEOSIDES; OLIGORIBONUCLEOTIDES
Erscheinungsdatum: 2013
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 78
Ausgabe: 17
Startseite: 8545
Seitenende: 8561
Zusammenfassung: 
Internal sugar cross-links were introduced for the first time into oligonucleotides with parallel chain orientation by click ligation. For this, the 2'- or 3'-position of the isoguanosine ribose moiety was functionalized with clickable propargyl residues, and the synthesis of propargylated cytosine building blocks was significantly improved. Phosphoramidites were prepared and employed in solid-phase synthesis. A series of oligo-2'-deoxyribonucleotides with parallel (ps) and antiparallel (aps) strand orientation were constructed containing isoguanine-cytosine, isoguanine-isocytosine, and adeninethymine base pairs. Complementary oligonucleotides with propargylated sugar residues were ligated in a stepwise manner with a chelating bis-azide under copper catalysis. Cross-links were introduced within a base pair or in positions separated by two base pairs. From T-m stability studies it is evident that cross-linking stabilizes DNA with parallel strand orientation strongly (Delta T-m from 16 to 18.5 degrees C) with a similar increase as for aps DNA.
ISSN: 00223263
DOI: 10.1021/jo4012706

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