Literature DB >> 23553943

New RNA purine building blocks, 4'-selenopurine nucleosides: first synthesis and unusual mixture of sugar puckerings.

Jinha Yu1, Jin-Hee Kim, Hyuk Woo Lee, Varughese Alexander, Hee-Chul Ahn, Won Jun Choi, Jungwon Choi, Lak Shin Jeong.   

Abstract

Writer's blocks: The first synthesis of RNA purine building blocks, 4'-selenoadenosine and 4'-selenoguanosine was achieved from D-ribose by regioisomeric rearrangement, which was confirmed by X-ray crystallography. 4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID: 23553943     DOI: 10.1002/chem.201300741

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  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

2.  When nucleoside chemistry met hypervalent iodine reagents.

Authors:  Mahesh K Lakshman; Barbara Zajc
Journal:  ARKIVOC       Date:  2017-12-21       Impact factor: 1.140

3.  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 4.  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 5.  The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold.

Authors:  Katherine L Seley-Radtke; Mary K Yates
Journal:  Antiviral Res       Date:  2018-04-10       Impact factor: 10.103

Review 6.  Zero-, one-, two- and three-dimensional supramolecular architectures sustained by SeO chalcogen bonding: A crystallographic survey.

Authors:  Edward R T Tiekink
Journal:  Coord Chem Rev       Date:  2020-10-17       Impact factor: 22.315

7.  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
  7 in total

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