Site-Specific Covalent Modification of RNA Guided by Functionality-Transfer Oligodeoxynucleotides

被引：39

作者：

Onizuka, Kazumitsu

Taniguchi, Yosuke

Sasaki, Shigeki

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Fukuoka 8128582, Japan

[2] Japan Sci & Technol Agcy, CREST, Kawaguchi, Saitama 3320012, Japan

来源：

BIOCONJUGATE CHEMISTRY | 2009年 / 20卷 / 04期

基金：

日本科学技术振兴机构; 日本学术振兴会;

关键词：

CROSS-LINKING; CYTIDINE; ALKYLATION; ACTIVATION; EFFICIENT; STRATEGY; DNA;

D O I：

10.1021/bc900009p

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Efficient methods for the covalent modification of large RNA molecules should find significance utility as innovative biological tools as well as therapeutic methods. In this study, the development of a general method for site-specific RNA modification guided by the functional ODN template has been investigated. The ODN probe containing 6-thioguanosine was modified by the methylenediketone derivative to form the S-functionalized ODN. Site-specific and cytosine-selective RNA modifications were achieved by the functionality-transfer reaction from the sulfur atom of the functionalized probe to the amino group of the cytosine base of the target strand. It was shown that the base and site selectivity were due to the close proximity of the reactants in the DNA-RNA duplexes.

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收藏

页码：799 / 803

页数：5

相关论文

共 15 条

[1] Sequence- and base-specific delivery of nitric oxide to cytidine and 5-methylcytidine leading to efficient deamination [J].

Ali, M ;

Alam, R ;

Kawasaki, T ;

Nakayama, S ;

Nagatsugi, F ;

Sasaki, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :8864-8865

[2] Intracellular inducible alkylation system that exhibits antisense effects with greater potency and selectivity than the natural oligonucleotide [J].

Ali, Md. Monsur ;

Oishi, Motoi ;

Nagatsugi, Fumi ;

Mori, Kenya ;

Nagasaki, Yukio ;

Kataoka, Kazunori ;

Sasaki, Shigeki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3136-3140

[3] Deoxyribozyme-catalyzed labeling of RNA [J].

Baum, Dana A. ;

Silverman, Scott K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3502-3504

[4] Combined approaches to site-specific modification of RNA [J].

Chow, Christine S. ;

Mahto, Santosh K. ;

Lamichhane, Tek N. .

ACS CHEMICAL BIOLOGY, 2008, 3 (01) :30-37

[5] EVIDENCE FROM CD-SPECTRA THAT D(PURINE)CENTER-DOT-R(PYRIMIDINE) AND R(PURINE)CENTER-DOT-D(PYRIMIDINE) HYBRIDS ARE IN DIFFERENT STRUCTURAL CLASSES [J].

HUNG, SH ;

YU, Q ;

GRAY, DM ;

RATLIFF, RL .

NUCLEIC ACIDS RESEARCH, 1994, 22 (20) :4326-4334

[6] Site-specific fluorescent labeling of RNA molecules by specific transcription using unnatural base pairs [J].

Kawai, R ;

Kimoto, M ;

Ikeda, S ;

Mitsui, T ;

Endo, M ;

Yokoyama, S ;

Hirao, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17286-17295

[7] Hybridization-promoted and cytidine-selective activation for cross-linking with the use of 2-amino-6-vinylpurine derivatives [J].

Kawasaki, T ;

Nagatsugi, F ;

Ali, MM ;

Maeda, M ;

Sugiyama, K ;

Hori, K ;

Sasaki, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :14-23

[8] INTERACTION OF PSORALEN-DERIVATIZED OLIGODEOXYRIBONUCLEOSIDE METHYLPHOSPHONATES WITH SINGLE-STRANDED-DNA [J].

LEE, BL ;

MURAKAMI, A ;

BLAKE, KR ;

LIN, SB ;

MILLER, PS .

BIOCHEMISTRY, 1988, 27 (09) :3197-3203

[9] Oxovanadium complex-catalyzed aerobic oxidation of propargylic alcohols [J].

Maeda, Y ;

Kakiuchi, N ;

Matsumura, S ;

Nishimura, T ;

Kawamura, T ;

Uemura, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) :6718-6724

[10] Highly efficient and selective cross-linking to cytidine based on a new strategy for auto-activation within a duplex [J].

Nagatsugi, F ;

Kawasaki, T ;

Usui, D ;

Maeda, M ;

Sasaki, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6753-6754