Protected 5-(hydroxymethyl) uracil nucleotides bearing
visible-light photocleavable groups as building blocks for
polymerase synthesis of photocaged DNA

J 2018

Protected 5-(hydroxymethyl) uracil nucleotides bearing visible-light photocleavable groups as building blocks for polymerase synthesis of photocaged DNA

BOHACOVA, Sona, Lucie LUDVÍKOVÁ, Lenka SLAVETINSKA POSTOVA, Zuzana VANIKOVA, Petr KLÁN et. al.

Basic information

Original name

Protected 5-(hydroxymethyl) uracil nucleotides bearing visible-light photocleavable groups as building blocks for polymerase synthesis of photocaged DNA

Authors

BOHACOVA, Sona (203 Czech Republic), Lucie LUDVÍKOVÁ (203 Czech Republic, belonging to the institution), Lenka SLAVETINSKA POSTOVA (203 Czech Republic), Zuzana VANIKOVA (203 Czech Republic), Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution) and Michal HOCEK (203 Czech Republic)

Edition

ORGANIC & BIOMOLECULAR CHEMISTRY, CAMBRIDGE (ENGLAND), ROYAL SOC CHEMISTRY, 2018, 1477-0520

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.490

RIV identification code

RIV/00216224:14310/18:00100981

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1039/c8ob00160j

UT WoS

000429266600015

Keywords in English

STEM-CELL DNA; RESTRICTION ENDONUCLEASES; MAMMALIAN-CELLS; RNA-POLYMERASE; CHEMICAL-MODIFICATIONS; PHOTOCHEMICAL CONTROL; GENE-EXPRESSION; NUCLEIC-ACIDS; MODIFIED BASE; TRANSCRIPTION

Abstract

V originále

Nucleosides, nucleotides and 2'-deoxyribonucleoside triphosphates (dNTPs) containing 5-(hydroxy-methyl) uracil protected with photocleavable groups (2-nitrobenzyl-, 6-nitropiperonyl or 9-anthrylmethyl) were prepared and tested as building blocks for the polymerase synthesis of photocaged oligonucleotides and DNA. Photodeprotection (photorelease) reactions were studied in detail on model nucleoside mono-phosphates and their photoreaction quantum yields were determined. Photocaged dNTPs were then tested and used as substrates for DNA polymerases in primer extension or PCR. DNA probes containing photocaged or free 5-hydroxymethylU in the recognition sequence of restriction endonucleases were prepared and used for the study of photorelease of caged DNA by UV or visible light at different wavelengths. The nitropiperonyl-protected nucleotide was found to be a superior building block because the corresponding dNTP is a good substrate for DNA polymerases, and the protecting group is efficiently cleavable by irradiation by UV or visible light (up to 425 nm).

Links

GA13-25775S, research and development project

Name: Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

Investor: Czech Science Foundation

LM2011028, research and development project

Name: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

BOHACOVA, Sona, Lucie LUDVÍKOVÁ, Lenka SLAVETINSKA POSTOVA, Zuzana VANIKOVA, Petr KLÁN and Michal HOCEK. Protected 5-(hydroxymethyl) uracil nucleotides bearing visible-light photocleavable groups as building blocks for polymerase synthesis of photocaged DNA. ORGANIC & BIOMOLECULAR CHEMISTRY. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2018, vol. 16, No 9, p. 1527-1535. ISSN 1477-0520. Available from: https://dx.doi.org/10.1039/c8ob00160j.

@article{1419444,
   author = {Bohacova, Sona and Ludvíková, Lucie and Slavetinska Postova, Lenka and Vanikova, Zuzana and Klán, Petr and Hocek, Michal},
   article_location = {CAMBRIDGE (ENGLAND)},
   article_number = {9},
   doi = {http://dx.doi.org/10.1039/c8ob00160j},
   keywords = {STEM-CELL DNA; RESTRICTION ENDONUCLEASES; MAMMALIAN-CELLS; RNA-POLYMERASE; CHEMICAL-MODIFICATIONS; PHOTOCHEMICAL CONTROL; GENE-EXPRESSION; NUCLEIC-ACIDS; MODIFIED BASE; TRANSCRIPTION},
   language = {eng},
   issn = {1477-0520},
   journal = {ORGANIC & BIOMOLECULAR CHEMISTRY},
   title = {Protected 5-(hydroxymethyl) uracil nucleotides bearing visible-light photocleavable groups as building blocks for polymerase synthesis of photocaged DNA},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C8OB00160J#!divAbstract},
   volume = {16},
   year = {2018}
}

TY  - JOUR
ID  - 1419444
AU  - Bohacova, Sona - Ludvíková, Lucie - Slavetinska Postova, Lenka - Vanikova, Zuzana - Klán, Petr - Hocek, Michal
PY  - 2018
TI  - Protected 5-(hydroxymethyl) uracil nucleotides bearing visible-light photocleavable groups as building blocks for polymerase synthesis of photocaged DNA
JF  - ORGANIC & BIOMOLECULAR CHEMISTRY
VL  - 16
IS  - 9
SP  - 1527-1535
EP  - 1527-1535
PB  - ROYAL SOC CHEMISTRY
SN  - 14770520
KW  - STEM-CELL DNA
KW  - RESTRICTION ENDONUCLEASES
KW  - MAMMALIAN-CELLS
KW  - RNA-POLYMERASE
KW  - CHEMICAL-MODIFICATIONS
KW  - PHOTOCHEMICAL CONTROL
KW  - GENE-EXPRESSION
KW  - NUCLEIC-ACIDS
KW  - MODIFIED BASE
KW  - TRANSCRIPTION
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C8OB00160J#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C8OB00160J#!divAbstract
N2  - Nucleosides, nucleotides and 2'-deoxyribonucleoside triphosphates (dNTPs) containing 5-(hydroxy-methyl) uracil protected with photocleavable groups (2-nitrobenzyl-, 6-nitropiperonyl or 9-anthrylmethyl) were prepared and tested as building blocks for the polymerase synthesis of photocaged oligonucleotides and DNA. Photodeprotection (photorelease) reactions were studied in detail on model nucleoside mono-phosphates and their photoreaction quantum yields were determined. Photocaged dNTPs were then tested and used as substrates for DNA polymerases in primer extension or PCR. DNA probes containing photocaged or free 5-hydroxymethylU in the recognition sequence of restriction endonucleases were prepared and used for the study of photorelease of caged DNA by UV or visible light at different wavelengths. The nitropiperonyl-protected nucleotide was found to be a superior building block because the corresponding dNTP is a good substrate for DNA polymerases, and the protecting group is efficiently cleavable by irradiation by UV or visible light (up to 425 nm).
ER  -

BOHACOVA, Sona, Lucie LUDVÍKOVÁ, Lenka SLAVETINSKA POSTOVA, Zuzana VANIKOVA, Petr KLÁN and Michal HOCEK. Protected 5-(hydroxymethyl) uracil nucleotides bearing visible-light photocleavable groups as building blocks for polymerase synthesis of photocaged DNA. \textit{ORGANIC \&{}amp; BIOMOLECULAR CHEMISTRY}. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2018, vol.~16, No~9, p.~1527-1535. ISSN~1477-0520. Available from: https://dx.doi.org/10.1039/c8ob00160j.

Detailed Information on Publication Record