A new strategy for the solid-phase synthesis of 5′-thiolated oligodeoxynucleotides
A novel procedure is described for the introduction of a masked thiol function at the 5′-terminus of oligodeoxynucleotides. An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleotides using standard solid-phase techniques. O...
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Published in | Tetrahedron Vol. 49; no. 47; pp. 10931 - 10944 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
1993
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | A novel procedure is described for the introduction of a masked thiol function at the 5′-terminus of oligodeoxynucleotides. An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleotides using standard solid-phase techniques. Our strategy is elaborated for oligothymidylates and is further illustrated for oligodeoxynucleotides which are base-protected with the 2-(acetoxymethyl)benzoyl group. Rapid base-deprotection can be accomplished in methanolic potassium carbonate which also effects saponification of the thioacetyl ester. The resultant free thiol is reacted
in situ with dithiodipyridine to afford pyridyldisulfide-derivatized oligodeoxynucleotides.
The preparation of a thioacetyl linker phosphoramidite is described which enables the introduction of a pyridyldisulfide function at the 5′-terminus of oligodeoxynucleotides. |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/S0040-4020(01)80247-7 |