Efficient Solid Phase Synthesis of Cleavable Oligodeoxynucleotides Based on a Novel Strategy for the Synthesis of 5′-S-(4,4′-Dimethoxytrityl)-2′-deoxy-5′-thionucleoside Phosphoramidites

• Published in: Helvetica chimica acta Vol. 87; no. 11; pp. 2812 - 2828
• Main Authors: Jahn-Hofmann, Kerstin, Engels, Joachim W.
• Format: Journal Article
• Language: English
• Published: Zürich WILEY-VCH Verlag 01.11.2004; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; ATTACHMENT; RNA; ANALOGS; DNA; NUCLEOSIDES; OLIGODEOXYRIBONUCLEOTIDES; LINKAGE; THIOL SPECIFIC PROBES; OLIGONUCLEOTIDES
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.200490252

The incorporation of a specific cleavage site into an oligodeoxynucleotide can be achieved by utilizing the four 5′‐S‐(4,4′‐dimethoxytrityl)‐2′‐deoxy‐5′‐thionucleoside 3′‐(2‐cyanoethyl diisopropylphosphoramidites) 5 and 15a–c (Fig. 1). Based on the silver ion assisted cleavage of PS and CS bonds, we synthesized oligodeoxynucleotides with an achiral 5′‐phosphorothioate linkage 3′–O–P–S–5′ by the solid‐phase phosphoramidite procedure. The efficient cleavage of these modified oligodeoxynucleotides can be detected by HPLC, PAGE, and surface plasmon resonance (SPR) spectrometry. The liberated 5′‐thiol moiety can be used directly for post‐reaction labeling with appropriately functionalized reporter groups.