Synthesis of a 2‐Selenothymidine Phosphoramidite and Its Incorporation into Oligodeoxyribonucleotides
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- Abstract
- Table of Contents
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Abstract
The detailed synthetic protocol for a 2?selenothymidine phosphoramidite and its use in preparing Se?derivatized oligonucleotides are described here. The Se?modified phosphoramidite synthesis was achieved by activating a 2?thiothymidine derivative, followed by introduction of selenium functionality. The coupling reaction yield of the 2?selenothymidine phosphoramidite during solid?phase synthesis is high (>95%), and the oligonucleotides containing the 2?selenothymidine derivatization are stable. Curr. Protoc. Nucleic Acid Chem. 42:1.23.1?1.23.13. © 2010 by John Wiley & Sons, Inc.
Keywords: nucleic acid; selenium; derivatization; base pairing; X?ray crystallography
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- Introduction
- Basic Protocol 1: Preparation of the 2‐Selenothymidine Phosphoramidite
- Support Protocol 1: Synthesis of Iodopropionitrile
- Basic Protocol 2: Synthesis, Purification, and Characterization of Oligonucleotides Containing 2‐Selenothymidine
- Commentary
- Literature Cited
- Figures
- Tables
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Basic Protocol 1: Preparation of the 2‐Selenothymidine Phosphoramidite
Materials
Support Protocol 1: Synthesis of Iodopropionitrile
Materials
Basic Protocol 2: Synthesis, Purification, and Characterization of Oligonucleotides Containing 2‐Selenothymidine
Materials
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Figure 1.23.1 Synthetic scheme of the 2‐selenothymidine phosphoramidite (S.6 ) and the Se‐DNAs (S.7 ). View Image -
Figure 1.23.2 MALDI‐TOF mass spectrum of 2Se‐T 9‐mer (5′‐ATGGSeTGCTC‐3′); C88 H104 N32 O53 P8 Se, calculated: 2794.8, observed: 2794.2. View Image -
Figure 1.23.3 UV melting curves. (A ) Duplex of native DNAs 5′‐CTTCTTGTCCG‐3′ and 5′‐CGGACAAGAAG‐3′ ( T m = 42.6°C). (B ) Duplex of Se‐DNA 5′‐CTTCTTSe GTCCG‐3′ and native DNA 5′‐CGGACAACAAC‐3′ ( T m = 42.2°C). View Image
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Literature Cited
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