Next Article in Journal
Antibacterial Effects of the Essential Oils of Commonly Consumed Medicinal Herbs Using an In Vitro Model
Next Article in Special Issue
Selenol Protecting Groups in Organic Chemistry: Special Emphasis on Selenocysteine Se-Protection in Solid Phase Peptide Synthesis
Previous Article in Journal
Synthesis of New Azo Compounds Based on N-(4-Hydroxypheneyl)maleimide and N-(4-Methylpheneyl)maleimide
Previous Article in Special Issue
Protecting Groups in Carbohydrate Chemistry: Influence on Stereoselectivity of Glycosylations
Molecules 2010, 15(11), 7509-7531; doi:10.3390/molecules15117509
Article

Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3′-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N3-Cyano-Ethylthymine

,
,
,
 and *
Received: 27 August 2010; in revised form: 8 October 2010 / Accepted: 14 October 2010 / Published: 27 October 2010
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
Download PDF [473 KB, uploaded 18 June 2014]
Abstract: Oligodeoxynucleotide (ODN) synthesis, which avoids the formation of side products, is of great importance to biochemistry-based technology development. One side reaction of ODN synthesis is the cyanoethylation of the nucleobases. We suppressed this reaction by synthesizing ODNs using fully protected deoxynucleoside 3′-phosphoramidite building blocks, where the remaining reactive nucleobase residues were completely protected with acyl-, diacyl-, and acyl-oxyethylene-type groups. The detailed analysis of cyanoethylation at the nucleobase site showed that N3-protection of the thymine base efficiently suppressed the Michael addition of acrylonitrile. An ODN incorporating N3-cyanoethylthymine was synthesized using the phosphoramidite method, and primer extension reactions involving this ODN template were examined. As a result, the modified thymine produced has been proven to serve as a chain terminator.
Keywords: protecting group; oligodeoxynucleotide synthesis; cyanoethylation protecting group; oligodeoxynucleotide synthesis; cyanoethylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Tsunoda, H.; Kudo, T.; Ohkubo, A.; Seio, K.; Sekine, M. Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3′-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N3-Cyano-Ethylthymine. Molecules 2010, 15, 7509-7531.

AMA Style

Tsunoda H, Kudo T, Ohkubo A, Seio K, Sekine M. Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3′-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N3-Cyano-Ethylthymine. Molecules. 2010; 15(11):7509-7531.

Chicago/Turabian Style

Tsunoda, Hirosuke; Kudo, Tomomi; Ohkubo, Akihiro; Seio, Kohji; Sekine, Mitsuo. 2010. "Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3′-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N3-Cyano-Ethylthymine." Molecules 15, no. 11: 7509-7531.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert