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.

Základní údaje

Originální název

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

Autoři

BOHACOVA, Sona; Lucie LUDVÍKOVÁ; Lenka SLAVETINSKA POSTOVA; Zuzana VANIKOVA; Petr KLÁN a Michal HOCEK

Vydání

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

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.490

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/18:00100981

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

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

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 3. 6. 2018 12:59, Mgr. Michaela Hylsová, Ph.D.

Anotace

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).

Návaznosti

GA13-25775S, projekt VaV

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

Investor: Grantová agentura ČR, Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

LM2011028, projekt VaV

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

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX Národní infrastruktura pro výzkum toxických látek v prostředí

LO1214, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Centrum pro výzkum toxických látek v prostředí

Citovat

BOHACOVA, Sona; Lucie LUDVÍKOVÁ; Lenka SLAVETINSKA POSTOVA; Zuzana VANIKOVA; Petr KLÁN a 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, roč. 16, č. 9, s. 1527-1535. ISSN 1477-0520. Dostupné z: https://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 = {https://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 a 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, roč.~16, č.~9, s.~1527-1535. ISSN~1477-0520. Dostupné z: https://doi.org/10.1039/c8ob00160j.

Přehled o publikaci