Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties

Mariko Aso; Yasuhiro Matsui; Bo Yang; Midori Sasagaki; Daiki Okado; Kazuteru Usui; Noboru Koga; Hiroshi Suemune

doi:10.1016/j.tet.2015.05.080

Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties

Mariko Aso, Yasuhiro Matsui, Bo Yang, Midori Sasagaki, Daiki Okado, Kazuteru Usui, Noboru Koga, Hiroshi Suemune

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine.

Original language	English
Pages (from-to)	5414-5419
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2015.05.080
Publication status	Published - Jul 11 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2015.05.080

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title = "Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties",

abstract = "5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine.",

author = "Mariko Aso and Yasuhiro Matsui and Bo Yang and Midori Sasagaki and Daiki Okado and Kazuteru Usui and Noboru Koga and Hiroshi Suemune",

note = "Funding Information: This work was partly supported by JSPS KAKENHI Grant Number 15590012 . We are also grateful for Prof. Ken-ichi Yamada (Kyushu university) for fruitful discussion. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

year = "2015",

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day = "11",

doi = "10.1016/j.tet.2015.05.080",

language = "English",

volume = "71",

pages = "5414--5419",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties

AU - Aso, Mariko

AU - Matsui, Yasuhiro

AU - Yang, Bo

AU - Sasagaki, Midori

AU - Okado, Daiki

AU - Usui, Kazuteru

AU - Koga, Noboru

AU - Suemune, Hiroshi

N1 - Funding Information: This work was partly supported by JSPS KAKENHI Grant Number 15590012 . We are also grateful for Prof. Ken-ichi Yamada (Kyushu university) for fruitful discussion. Publisher Copyright: © 2015 Elsevier Ltd. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2015/7/11

Y1 - 2015/7/11

N2 - 5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine.

AB - 5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine.

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U2 - 10.1016/j.tet.2015.05.080

DO - 10.1016/j.tet.2015.05.080

M3 - Article

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VL - 71

SP - 5414

EP - 5419

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 33

ER -

Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties

Abstract

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