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

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

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Oxford University Press
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PMC
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  • Biology
  • Chemistry
  • Medicine
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Abstract

gkl1091 1222..1229 1222–1229 Nucleic Acids Research, 2007, Vol. 35, No. 4 Published online 2 January 2007 doi:10.1093/nar/gkl1091 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 Received November 10, 2006; Revised November 23, 2006; Accepted November 29, 2006 ABSTRACT The boronic acid moiety is a versatile functional group useful in carbohydrate recognition, glycopro- tein 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 poly- merization, 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. INTRODUCTION Boronic acid is a versatile functional group that has been explored for the development of various biologically important compounds (1–3), such as carbohydrat

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