Cross-Linked DNA: Propargylated Ribonucleosides as “Click” Ligation Sites for Bifunctional Azides

• Published in: Journal of organic chemistry Vol. 77; no. 9; pp. 4460 - 4465
• Main Authors: Pujari, Suresh S, Seela, Frank
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.05.2012; Amer Chemical Soc
• Subjects: Aliphatic compounds; Analytical, structural and metabolic biochemistry; Azides - chemistry; Base Sequence; Biological and medical sciences; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Cross-Linking Reagents; DNA - chemistry; Dna, deoxyribonucleoproteins; DNA, Single-Stranded - chemistry; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Ligation; Magnetic Resonance Spectroscopy; Molecular Structure; Nucleic acids; Nucleosides, nucleotides and oligonucleotides; Oligonucleotides - chemistry; Organic chemistry; Pargyline - analogs & derivatives; Pargyline - chemistry; Physical Sciences; Preparations and properties; Ribonucleosides - chemistry; Science & Technology; DOUBLE-HELIX; LINKING; CONJUGATION; DUPLEX STABILITY; ADENOSINE-DEAMINASE; BASE-PAIRS; CHEMISTRY; TERMINAL ALKYNES; HYBRIDIZATION; OLIGONUCLEOTIDES; Adenosine; Acetylenic compound; Organic azide; Aliphatic compound; Bifunctional compound; Propargylic compound; Oside; Crosslinking; Hybridization; chemical ligation; Duplex; Azides; Crosslinked state; DNA; Nucleoside; Aromatic compound; Click chemistry; Ribonucleoside
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo300421p

2′-O or 3′-O-propargylated adenosines and ribothymidines were used as click targets for cross-linking of oligonucleotides with aliphatic and aromatic azides. The cross-link generates a sugar modification at the 2′-O-ligation site. Inexpensive ribonucleosides were used as starting materials. Cross-linking of oligonucleotides was performed at internal or terminal positions. Hybridization of homodimers with two complementary single strands resulted in stable ligated DNA duplexes.