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Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase

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,...

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Autores principales: Tauraitė, Daiva, Jakubovska, Jevgenija, Dabužinskaitė, Julija, Bratchikov, Maksim, Meškys, Rolandas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154577/
https://www.ncbi.nlm.nih.gov/pubmed/28441732
http://dx.doi.org/10.3390/molecules22040672
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author Tauraitė, Daiva
Jakubovska, Jevgenija
Dabužinskaitė, Julija
Bratchikov, Maksim
Meškys, Rolandas
author_facet Tauraitė, Daiva
Jakubovska, Jevgenija
Dabužinskaitė, Julija
Bratchikov, Maksim
Meškys, Rolandas
author_sort Tauraitė, Daiva
collection PubMed
description 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 N(4)-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.
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spelling pubmed-61545772018-11-13 Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase Tauraitė, Daiva Jakubovska, Jevgenija Dabužinskaitė, Julija Bratchikov, Maksim Meškys, Rolandas Molecules Communication 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 N(4)-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. MDPI 2017-04-22 /pmc/articles/PMC6154577/ /pubmed/28441732 http://dx.doi.org/10.3390/molecules22040672 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Tauraitė, Daiva
Jakubovska, Jevgenija
Dabužinskaitė, Julija
Bratchikov, Maksim
Meškys, Rolandas
Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase
title Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase
title_full Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase
title_fullStr Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase
title_full_unstemmed Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase
title_short Modified Nucleotides as Substrates of Terminal Deoxynucleotidyl Transferase
title_sort modified nucleotides as substrates of terminal deoxynucleotidyl transferase
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154577/
https://www.ncbi.nlm.nih.gov/pubmed/28441732
http://dx.doi.org/10.3390/molecules22040672
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