Journal of Organic Chemistry

, volume 77 , issue 2 , pages 977-984

4′,5′-Dichloro-2′,7′-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and Spectral Properties of Oligonucleotide Conjugates

Dmitry A Tsybulsky ¹

Maksim V Kvach ¹

Irina A Stepanova ²

Vladimir A. Korshun ²

V.V. Shmanai ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Institute of Physical Organic Chemistry, Surganova 13, 220072 Minsk, Belarus |

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, 117997 Moscow, Russia |

Publication type: Journal Article

Publication date: 2011-12-23

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/jo202229t

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PubMed ID: 22148236

Organic Chemistry

Abstract

A convenient procedure for the preparation of the fluorescent dye 4',5'-dichloro-2',7'-dimethoxy-5(6)-carboxyfluorescein (JOE) is reported; the overall yield achieved starting from isovanillin is 10 times higher (40% vs 4%) compared to the known procedure. Isomers (5- and 6-) are easily chromatographically separable as pentafluorophenyl esters of 3',6'-O-bis(cyclohexylcarbonyl) derivatives. Four non-nucleoside JOE phosphoramidites based on 5- and 6-isomers and flexible 6-aminohexanol (AH) or rigid 4-trans-aminocyclohexanol (ACH) linkers have been prepared and used for oligonucleotide labeling. Spectral and photophysical properties of 5'-JOE-modified oligonucleotides have been studied. Fluorescence quantum yield of the dye correlates with the nature of the linker (rigid vs flexible) and with the presence of dG nucleosides in close proximity to a JOE residue.

Found

1 citation

Golovin Andrey

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DSc in Chemistry

98 publications, 1 339 citations

h-index: 20

Lomonosov Moscow State University

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

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Tsybulsky D. A. et al. 4′,5′-Dichloro-2′,7′-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and Spectral Properties of Oligonucleotide Conjugates // Journal of Organic Chemistry. 2011. Vol. 77. No. 2. pp. 977-984.

GOST all authors (up to 50) Copy

Tsybulsky D. A., Kvach M. V., Stepanova I. A., Korshun V. A., Shmanai V. 4′,5′-Dichloro-2′,7′-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and Spectral Properties of Oligonucleotide Conjugates // Journal of Organic Chemistry. 2011. Vol. 77. No. 2. pp. 977-984.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/jo202229t

UR - https://doi.org/10.1021/jo202229t

TI - 4′,5′-Dichloro-2′,7′-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and Spectral Properties of Oligonucleotide Conjugates

T2 - Journal of Organic Chemistry

AU - Tsybulsky, Dmitry A

AU - Kvach, Maksim V

AU - Stepanova, Irina A

AU - Korshun, Vladimir A.

AU - Shmanai, V.V.

PY - 2011

DA - 2011/12/23

PB - American Chemical Society (ACS)

SP - 977-984

IS - 2

VL - 77

PMID - 22148236

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2011_Tsybulsky,

author = {Dmitry A Tsybulsky and Maksim V Kvach and Irina A Stepanova and Vladimir A. Korshun and V.V. Shmanai},

title = {4′,5′-Dichloro-2′,7′-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and Spectral Properties of Oligonucleotide Conjugates},

journal = {Journal of Organic Chemistry},

year = {2011},

volume = {77},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/jo202229t},

number = {2},

pages = {977--984},

doi = {10.1021/jo202229t}

}

MLA

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MLA Copy

Tsybulsky, Dmitry A., et al. “4′,5′-Dichloro-2′,7′-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and Spectral Properties of Oligonucleotide Conjugates.” Journal of Organic Chemistry, vol. 77, no. 2, Dec. 2011, pp. 977-984. https://doi.org/10.1021/jo202229t.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)