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Nucleic Acids Research Advance Access originally published online on January 31, 2007
Nucleic Acids Research 2007 35(4):1222-1229; doi:10.1093/nar/gkl1091
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Nucleic Acids Research, 2007, Vol. 35, No. 4 1222-1229
© 2007 The Author(s).
This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Chemistry

Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA

Na Lin1, Jun Yan1, Zhen Huang1, Craig Altier2, Minyong Li1, Nicolas Carrasco1, Mitsu Suyemoto2, Lynette Johnston2, Siming Wang1, Qian Wang3, Hao Fang1, Julianne Caton-Williams1 and Binghe Wang1,*

1Department of Chemistry and Center for Biotechnology and Drug Design, Campus Box 4098, Georgia State University, Atlanta, GA 30302-4098, USA, 2College of Veterinary Medicine, North Carolina State University, 4700 Hillsborough St., Raleigh, NC 27606, USA and 3Department of Chemistry and Biochemistry, 631 Sumter St. University of South Carolina, Columbia, SC 29202, USA.

*To whom correspondence should be addressed. Tel: +1 404 651 0289; Fax: +1 404 654 5827; Email: wang{at}gsu.edu

Received November 10, 2006. Revised November 23, 2006. Accepted November 29, 2006.

The boronic acid moiety is a versatile functional group useful in carbohydrate recognition, glycoprotein pull-down, inhibition of hydrolytic enzymes and boron neutron capture therapy. The incorporation of the boronic-acid group into DNA could lead to molecules of various biological functions. We have successfully synthesized a boronic acid-labeled thymidine triphosphate (B-TTP) linked through a 14-atom tether and effectively incorporated it into DNA by enzymatic polymerization. The synthesis was achieved using the Huisgen cycloaddition as the key reaction. We have demonstrated that DNA polymerase can effectively recognize the boronic acid-labeled DNA as the template for DNA polymerization, that allows PCR amplification of boronic acid-labeled DNA. DNA polymerase recognitions of the B-TTP as a substrate and the boronic acid-labeled DNA as a template are critical issues for the development of DNA-based lectin mimics via in vitro selection.


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