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Literature DB >> 27447361

Synthesis of Oligodeoxynucleotides Containing Electrophilic Groups.

Xi Lin¹, Jinsen Chen¹, Shahien Shahsavari¹, Nathanael Green¹, Deepti Goyal¹, Shiyue Fang¹.

Abstract

By use of 1,3-dithian-2-yl-methoxycarbonyl (Dmoc) as a protecting group and linker for oligodeoxynucleotide (ODN) synthesis, deprotection and cleavage are achieved under non-nucleophilic oxidative conditions. The nucleophile-sensitive thioester and α-chloroacetyl groups are conveniently incorporated into ODN sequences. The technology could be universally useful for electrophilic ODN synthesis.

Entities: Chemical Disease Species

Mesh：

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Year: 2016 PMID： 27447361 PMCID： PMC4975647 DOI： 10.1021/acs.orglett.6b01878

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

1. Hydroquinone-O,O'-diacetic acid ('Q-linker') as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis.

Authors: R T Pon; S Yu
Journal: Nucleic Acids Res Date: 1997-09-15 Impact factor: 16.971

2. Tet-mediated formation of 5-carboxylcytosine and its excision by TDG in mammalian DNA.

Authors: Yu-Fei He; Bin-Zhong Li; Zheng Li; Peng Liu; Yang Wang; Qingyu Tang; Jianping Ding; Yingying Jia; Zhangcheng Chen; Lin Li; Yan Sun; Xiuxue Li; Qing Dai; Chun-Xiao Song; Kangling Zhang; Chuan He; Guo-Liang Xu
Journal: Science Date: 2011-08-04 Impact factor: 47.728

3. Synthesis of oligonucleotides containing the alkali-labile pyrimidopurinone adduct, M(1)G.

Authors: N C Schnetz-Boutaud; H Mao; M P Stone; L J Marnett
Journal: Chem Res Toxicol Date: 2000-02 Impact factor: 3.739

4. Enhancement of selectivity in recognition of nucleic acids via chemical autoligation.

Authors: S M Gryaznov; R Schultz; S K Chaturvedi; R L Letsinger
Journal: Nucleic Acids Res Date: 1994-06-25 Impact factor: 16.971

5. RNA-protein binding interface in the telomerase ribonucleoprotein.

Authors: Christopher J Bley; Xiaodong Qi; Dustin P Rand; Chad R Borges; Randall W Nelson; Julian J-L Chen
Journal: Proc Natl Acad Sci U S A Date: 2011-11-28 Impact factor: 11.205

6. Comprehensive genome-wide protein-DNA interactions detected at single-nucleotide resolution.

Authors: Ho Sung Rhee; B Franklin Pugh
Journal: Cell Date: 2011-12-09 Impact factor: 41.582

7. Minor groove DNA alkylation directed by major groove triplex forming oligodeoxyribonucleotides.

Authors: E A Lukhtanov; A G Mills; I V Kutyavin; V V Gorn; M W Reed; R B Meyer
Journal: Nucleic Acids Res Date: 1997-12-15 Impact factor: 16.971

8. O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method.

Authors: Akihiro Ohkubo; Yusuke Ezawa; Kohji Seio; Mitsuo Sekine
Journal: J Am Chem Soc Date: 2004-09-08 Impact factor: 15.419

9. A novel combined chemical-enzymatic synthesis of cross-linked DNA using a nucleoside triphosphate analogue.

Authors: M Cowart; S J Benkovic
Journal: Biochemistry Date: 1991-01-22 Impact factor: 3.162

10. Site-specific incorporation of N-(deoxyguanosin-8-yl)-2-acetylaminofluorene (dG-AAF) into oligonucleotides using modified 'ultra-mild' DNA synthesis.

Authors: Ludovic C J Gillet; Jawad Alzeer; Orlando D Schärer
Journal: Nucleic Acids Res Date: 2005-04-06 Impact factor: 16.971

5 in total

Synthesis of Oligodeoxynucleotides Containing Electrophilic Groups.

1. Hydroquinone-O,O'-diacetic acid ('Q-linker') as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis.

2. Tet-mediated formation of 5-carboxylcytosine and its excision by TDG in mammalian DNA.

3. Synthesis of oligonucleotides containing the alkali-labile pyrimidopurinone adduct, M(1)G.

4. Enhancement of selectivity in recognition of nucleic acids via chemical autoligation.

5. RNA-protein binding interface in the telomerase ribonucleoprotein.

6. Comprehensive genome-wide protein-DNA interactions detected at single-nucleotide resolution.

7. Minor groove DNA alkylation directed by major groove triplex forming oligodeoxyribonucleotides.

8. O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method.

9. A novel combined chemical-enzymatic synthesis of cross-linked DNA using a nucleoside triphosphate analogue.

10. Site-specific incorporation of N-(deoxyguanosin-8-yl)-2-acetylaminofluorene (dG-AAF) into oligonucleotides using modified 'ultra-mild' DNA synthesis.

1. Dim and Dmoc Protecting Groups for Oligodeoxynucleotide Synthesis.

2. Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups.

3. dM-Dim for Carboxylic Acid Protection.

4. Linear Oligosulfoxides: Synthesis and Solubility Studies.

5. An amine protecting group deprotectable under nearly neutral oxidative conditions.