Literature DB >> 18088134

First synthesis of 4'-selenonucleosides showing unusual Southern conformation.

Lak Shin Jeong1, Dilip K Tosh, Hea Ok Kim, Ting Wang, Xiyan Hou, Ho Seop Yun, Youngjoo Kwon, Sang Kook Lee, Jungwon Choi, Long Xuan Zhao.   

Abstract

The first synthesis of 4'-selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4'-oxonucleosides were overwhelmed by the size of selenium and steric interactions, driving the conformation to the C2'-endo/ C3'-exo twist (Southern) conformation.

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Year:  2007        PMID： 18088134     DOI： 10.1021/ol7025558

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


  8 in total

1.  Synthesis of the tellurium-derivatized phosphoramidites and their incorporation into DNA oligonucleotides.

Authors:  Sibo Jiang; Jia Sheng; Zhen Huang
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2011-12

2.  N6-Substituted 5'-N-Methylcarbamoyl-4'-selenoadenosines as Potent and Selective A3 Adenosine Receptor Agonists with Unusual Sugar Puckering and Nucleobase Orientation.

Authors:  Jinha Yu; Long Xuan Zhao; Jongmi Park; Hyuk Woo Lee; Pramod K Sahu; Minghua Cui; Steven M Moss; Eva Hammes; Eugene Warnick; Zhan-Guo Gao; Minsoo Noh; Sun Choi; Hee-Chul Ahn; Jungwon Choi; Kenneth A Jacobson; Lak Shin Jeong
Journal:  J Med Chem       Date:  2017-04-19       Impact factor: 7.446

3.  Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides.

Authors:  Saúl Martínez-Montero; Susana Fernández; Yogesh S Sanghvi; Emmanuel A Theodorakis; Mervi A Detorio; Tamara R McBrayer; Tony Whitaker; Raymond F Schinazi; Vicente Gotor; Miguel Ferrero
Journal:  Bioorg Med Chem       Date:  2012-09-23       Impact factor: 3.641

4.  Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction.

Authors:  Luigia Serpico; Mauro De Nisco; Flavio Cermola; Michele Manfra; Silvana Pedatella
Journal:  Molecules       Date:  2021-04-27       Impact factor: 4.411

Review 5.  MLP (muscle LIM protein) as a stress sensor in the heart.

Authors:  Byambajav Buyandelger; Keat-Eng Ng; Snjezana Miocic; Izabela Piotrowska; Sylvia Gunkel; Ching-Hsin Ku; Ralph Knöll
Journal:  Pflugers Arch       Date:  2011-04-13       Impact factor: 3.657

Review 6.  Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates.

Authors:  Yuichi Yoshimura; Hideaki Wakamatsu; Yoshihiro Natori; Yukako Saito; Noriaki Minakawa
Journal:  Beilstein J Org Chem       Date:  2018-06-28       Impact factor: 2.883

Review 7.  Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues.

Authors:  Mieke Guinan; Caecilie Benckendorff; Mark Smith; Gavin J Miller
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411

8.  Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate.

Authors:  Michio Iwaoka; Yuta Hiyoshi; Shota Arai; Takeru Ito
Journal:  ACS Omega       Date:  2021-06-25
  8 in total

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