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Molecules 2017, 22(4), 672; doi:10.3390/molecules22040672

Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase

1
Department of Molecular Microbiology and Biotechnology, Institute of Biochemistry, Life Sciences Center, Vilnius University, Sauletekio al. 7, Vilnius LT-10257, Lithuania
2
Department of Physiology, Biochemistry, Microbiology and Laboratory Medicine, Faculty of Medicine, Vilnius University, M. K. Čiurlionio g. 21, Vilnius LT-03101, Lithuania
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Suzanne Peyrottes
Received: 16 March 2017 / Revised: 10 April 2017 / Accepted: 19 April 2017 / Published: 22 April 2017
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues)
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Abstract

The synthesis of novel modified nucleotides and their incorporation into DNA sequences opens many possibilities to change the chemical properties of oligonucleotides (ONs), and, therefore, broaden the field of practical applications of modified DNA. The chemical synthesis of nucleotide derivatives, including ones bearing thio-, hydrazino-, cyano- and carboxy groups as well as 2-pyridone nucleobase-containing nucleotides was carried out. The prepared compounds were tested as substrates of terminal deoxynucleotidyl transferase (TdT). The nucleotides containing N4-aminocytosine, 4-thiouracil as well as 2-pyridone, 4-chloro- and 4-bromo-2-pyridone as a nucleobase were accepted by TdT, thus allowing enzymatic synthesis of 3’-terminally modified ONs. The successful UV-induced cross-linking of 4-thiouracil-containing ONs to TdT was carried out. Enzymatic post-synthetic 3’-modification of ONs with various photo- and chemically-reactive groups opens novel possibilities for future applications, especially in analysis of the mechanisms of polymerases and the development of photo-labels, sensors, and self-assembling structures. View Full-Text
Keywords: terminal deoxynucleotidyl transferase; N4-amino-2’-deoxycytidine triphosphate; 4-thio-2’-deoxyuridine triphosphate; 4-bromo-2-pyridone; 4-chloro-2-pyridone; UV cross-linking terminal deoxynucleotidyl transferase; N4-amino-2’-deoxycytidine triphosphate; 4-thio-2’-deoxyuridine triphosphate; 4-bromo-2-pyridone; 4-chloro-2-pyridone; UV cross-linking
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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. (CC BY 4.0).

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MDPI and ACS Style

Tauraitė, D.; Jakubovska, J.; Dabužinskaitė, J.; Bratchikov, M.; Meškys, R. Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase. Molecules 2017, 22, 672.

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