Literature DB >> 24465059

Synthetic Routes to a Series of Proximal and Distal 2'-Deoxy Fleximers.

Orrette R Wauchope1, Melvin Velasquez1, Katherine Seley-Radtke1.   

Abstract

Two series of innovative 2'-deoxy nucleoside analogues have been designed where the nucleobase has been split into its imidazole and pyrimidine subunits. This structural modification serves to introduce flexibility into the nucleobase scaffold while still retaining the elements required for recognition. The synthetic efforts to realize these analogues are described within.

Entities:  

Keywords:  adenosine; flexible nucleosides; fleximers; guanosine; nucleobase; resistance

Year:  2012        PMID： 24465059      PMCID： PMC3898542          DOI： 10.1055/s-0032-1316791

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  23 in total

1.  "Fleximers". Design and synthesis of two novel split nucleosides.

Authors:  K L Seley; L Zhang; A Hagos
Journal:  Org Lett       Date:  2001-10-04       Impact factor: 6.005

Review 2.  A perspective on antiviral resistance.

Authors:  Paul D Griffiths
Journal:  J Clin Virol       Date:  2009-07-16       Impact factor: 3.168

3.  Substrate discrimination by the human GTP fucose pyrophosphorylase.

Authors:  Stephen Quirk; Katherine L Seley
Journal:  Biochemistry       Date:  2005-08-16       Impact factor: 3.162

4.  Purification to apparent homogeneity and properties of pig kidney L-fucose kinase.

Authors:  S H Park; I Pastuszak; R Drake; A D Elbein
Journal:  J Biol Chem       Date:  1998-03-06       Impact factor: 5.157

Review 5.  S-adenosylhomocysteine hydrolase inhibitors as broad-spectrum antiviral agents.

Authors:  E De Clercq
Journal:  Biochem Pharmacol       Date:  1987-08-15       Impact factor: 5.858

6.  Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants.

Authors:  Kalyan Das; Arthur D Clark; Paul J Lewi; Jan Heeres; Marc R De Jonge; Lucien M H Koymans; H Maarten Vinkers; Frederik Daeyaert; Donald W Ludovici; Michael J Kukla; Bart De Corte; Robert W Kavash; Chih Y Ho; Hong Ye; Mark A Lichtenstein; Koen Andries; Rudi Pauwels; Marie-Pierre De Béthune; Paul L Boyer; Patrick Clark; Stephen H Hughes; Paul A J Janssen; Eddy Arnold
Journal:  J Med Chem       Date:  2004-05-06       Impact factor: 7.446

Review 7.  Molecular basis of human immunodeficiency virus drug resistance: an update.

Authors:  Luis Menéndez-Arias
Journal:  Antiviral Res       Date:  2009-07-16       Impact factor: 5.970

8.  Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside.

Authors:  Katherine L Seley; Stephen Quirk; Samer Salim; Liang Zhang; Asmerom Hagos
Journal:  Bioorg Med Chem Lett       Date:  2003-06-16       Impact factor: 2.823

9.  High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: strategic flexibility explains potency against resistance mutations.

Authors:  Kalyan Das; Joseph D Bauman; Arthur D Clark; Yulia V Frenkel; Paul J Lewi; Aaron J Shatkin; Stephen H Hughes; Eddy Arnold
Journal:  Proc Natl Acad Sci U S A       Date:  2008-01-29       Impact factor: 11.205

10.  Identification of human L-fucose kinase amino acid sequence.

Authors:  Stephan Hinderlich; Markus Berger; Astrid Blume; Hao Chen; Darius Ghaderi; Christian Bauer
Journal:  Biochem Biophys Res Commun       Date:  2002-06-14       Impact factor: 3.575
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  11 in total

1.  Thiophene-expanded guanosine analogues of Gemcitabine.

Authors:  Zhe Chen; Therese C Ku; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem Lett       Date:  2015-07-30       Impact factor: 2.823

2.  "Reverse" carbocyclic fleximers: synthesis of a new class of adenosine deaminase inhibitors.

Authors:  Sarah C Zimmermann; Joshua M Sadler; Peter I O'Daniel; Nathaniel T Kim; Katherine L Seley-Radtke
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2013       Impact factor: 1.381

3.  Design, synthesis and evaluation of a series of acyclic fleximer nucleoside analogues with anti-coronavirus activity.

Authors:  Hannah L Peters; Dirk Jochmans; Adriaan H de Wilde; Clara C Posthuma; Eric J Snijder; Johan Neyts; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem Lett       Date:  2015-05-23       Impact factor: 2.823

Review 4.  Flexibility-Not just for yoga anymore!

Authors:  Katherine Seley-Radtke
Journal:  Antivir Chem Chemother       Date:  2018 Jan-Dec

5.  Flex-nucleoside analogues - Novel therapeutics against filoviruses.

Authors:  Mary K Yates; Mithun R Raje; Payel Chatterjee; Christina F Spiropoulou; Sina Bavari; Mike Flint; Veronica Soloveva; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem Lett       Date:  2017-04-22       Impact factor: 2.823

6.  Design and synthesis of a series of truncated neplanocin fleximers.

Authors:  Sarah C Zimmermann; Elizaveta O'Neill; Godwin U Ebiloma; Lynsey J M Wallace; Harry P De Koning; Katherine L Seley-Radtke
Journal:  Molecules       Date:  2014-12-16       Impact factor: 4.411

7.  Synthesis of distal and proximal fleximer base analogues and evaluation in the nucleocapsid protein of HIV-1.

Authors:  Therese Ku; Natalie Lopresti; Matthew Shirley; Mattia Mori; Jan Marchant; Xiao Heng; Maurizio Botta; Michael F Summers; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem       Date:  2019-05-15       Impact factor: 3.641

8.  Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity.

Authors:  Mary K Yates; Payel Chatterjee; Mike Flint; Yafet Arefeayne; Damjan Makuc; Janez Plavec; Christina F Spiropoulou; Katherine L Seley-Radtke
Journal:  Molecules       Date:  2019-09-02       Impact factor: 4.411

Review 9.  The evolution of antiviral nucleoside analogues: A review for chemists and non-chemists. Part II: Complex modifications to the nucleoside scaffold.

Authors:  Mary K Yates; Katherine L Seley-Radtke
Journal:  Antiviral Res       Date:  2018-12-08       Impact factor: 10.103

10.  An Expedient Synthesis of Flexible Nucleosides through Enzymatic Glycosylation of Proximal and Distal Fleximer Bases.

Authors:  Sophie Vichier-Guerre; Therese C Ku; Sylvie Pochet; Katherine L Seley-Radtke
Journal:  Chembiochem       Date:  2020-02-27       Impact factor: 3.461
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