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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
Author(s) -
JahnHofmann Kerstin,
Engels Joachim W.
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490252
Subject(s) - chemistry , phosphoramidite , cleavage (geology) , moiety , solid phase synthesis , combinatorial chemistry , thiol , surface plasmon resonance , stereochemistry , oligonucleotide , dna , organic chemistry , nanotechnology , biochemistry , peptide , nanoparticle , materials science , geotechnical engineering , fracture (geology) , engineering
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 PS and CS 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.