In:
Current Protocols in Nucleic Acid Chemistry, Wiley, Vol. 62, No. 1 ( 2015-09)
Abstract:
This unit describes the synthesis of 2′‐ O ‐methyldithiomethyluridine‐containing oligonucleotides, which can be deprotected to yield the parental oligoribonucleotides under high concentrations of glutathione similar in cytoplasm. The 2′‐ O ‐methyldithiomethyl group is sensitive to reductive conditions, so that it is incompatible to 3′‐ O ‐phosphoramidite modification in nucleosides. Thus, a novel post‐synthetic approach to obtain 2′‐ O ‐methyldithiomethyluridine‐containing oligonucleotides was developed, in which 2′‐ O ‐(2,4,6‐trimethoxybenzylthiomethyl)uridine‐modified oligonucleotides are readily converted by treatment with dimethyl(methylthio)sulfonium tetrafluoroborate to the 2′‐ O ‐methyldithiomethyluridine‐modified oligonucleotides. The 2′‐ O ‐methyldithiomethyluridine‐modified oligonucleotides are readily and cleanly converted to the parental oligonucleotides under high thiol conditions, such as 10 mM glutathione and dithiothreitol. © 2015 by John Wiley & Sons, Inc.
Type of Medium:
Online Resource
ISSN:
1934-9270
,
1934-9289
DOI:
10.1002/0471142700.2015.62.issue-1
DOI:
10.1002/0471142700.nc0463s62
Language:
English
Publisher:
Wiley
Publication Date:
2015
detail.hit.zdb_id:
2179070-X
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