Incorporation of 2′-deoxy-5-(trifluoromethyl)uridine and 5-cyano-2′-deoxyuridine into DNA

John C. Markley; Panadda Chirakul; Dina Sologub; Snorri Th Sigurdsson

doi:10.1016/S0960-894X(01)00461-9

Incorporation of 2′-deoxy-5-(trifluoromethyl)uridine and 5-cyano-2′-deoxyuridine into DNA

John C. Markley, Panadda Chirakul, Dina Sologub, Snorri Th Sigurdsson^*

^*Corresponding author for this work

Faculty of Physical Sciences

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

In an attempt to synthesize DNA containing 2′-deoxy-5-(trifluoromethyl)uridine (1) using previously published protocols, we found that the trifluoromethyl group converted into a cyano group, resulting in DNA containing 5-cyano-2′-deoxyuridine (3). We show that nucleoside 1 can be incorporated into DNA using phosphoramidite 2 in combination with acetyl-protected deoxycytidine and phenoxyacetyl-protected purine phosphoramidites. Replacing thymidine in DNA with 1 caused a slight decrease in DNA duplex stability at pH 6.9.

Original language	English
Pages (from-to)	2453-2455
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	18
DOIs	https://doi.org/10.1016/S0960-894X(01)00461-9
Publication status	Published - 17 Sept 2001

Bibliographical note

Funding Information:
We thank the National Institutes of Health (GM58914 and GM56947) for financial support, Dr. G. P. Drobny and E. A. Louie for helpful discussions, Dr. M. Sadilek for help with MS analyses and members of the Sigurdsson research group for critical reading of the manuscript.

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title = "Incorporation of 2′-deoxy-5-(trifluoromethyl)uridine and 5-cyano-2′-deoxyuridine into DNA",

abstract = "In an attempt to synthesize DNA containing 2′-deoxy-5-(trifluoromethyl)uridine (1) using previously published protocols, we found that the trifluoromethyl group converted into a cyano group, resulting in DNA containing 5-cyano-2′-deoxyuridine (3). We show that nucleoside 1 can be incorporated into DNA using phosphoramidite 2 in combination with acetyl-protected deoxycytidine and phenoxyacetyl-protected purine phosphoramidites. Replacing thymidine in DNA with 1 caused a slight decrease in DNA duplex stability at pH 6.9.",

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AU - Chirakul, Panadda

AU - Sologub, Dina

AU - Sigurdsson, Snorri Th

N1 - Funding Information: We thank the National Institutes of Health (GM58914 and GM56947) for financial support, Dr. G. P. Drobny and E. A. Louie for helpful discussions, Dr. M. Sadilek for help with MS analyses and members of the Sigurdsson research group for critical reading of the manuscript.

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Incorporation of 2′-deoxy-5-(trifluoromethyl)uridine and 5-cyano-2′-deoxyuridine into DNA

Abstract

Bibliographical note

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