Literature DB >> 20625456

Synthesis of Boranoate, Selenoate, and Thioate Analogs of AZTp(4)A and Ap(4)A.

Qianwei Han1, Stefan G Sarafianos, Eddy Arnold, Michael A Parniak, Barbara L Gaffney, Roger A Jones.   

Abstract

We report efficient, one-flask procedures for the synthesis of a family of fourteen analogs of AZTp(4)A and Ap(4)A containing BH(3), S, or Se, along with two bisphosphonate analogs of Ap(4)A. These compounds should slow unwanted enzymatic hydrolysis and have the potential to create unique binding interactions in biochemical and structural studies of the excision reaction responsible for resistance of HIV-1 to AZT, as well as assist in drug design.

Entities:  

Year:  2009        PMID： 20625456      PMCID： PMC2898137          DOI： 10.1016/j.tet.2009.07.079

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  24 in total

1.  3'-Azido-3'-deoxythymidine-(5')-tetraphospho-(5')-adenosine, the product of ATP-mediated excision of chain-terminating AZTMP, is a potent chain-terminating substrate for HIV-1 reverse transcriptase.

Authors:  Sanjeewa Dharmasena; Zita Pongracz; Eddy Arnold; Stefan G Sarafianos; Michael A Parniak
Journal:  Biochemistry       Date:  2007-01-23       Impact factor: 3.162

2.  Synthesis and resistance to enzymic hydrolysis of stereochemically-defined phosphonate and thiophosphate analogues of P1,P4-bis(5'-adenosyl) tetraphosphate.

Authors:  G M Blackburn; G E Taylor; G R Thatcher; M Prescott; A G McLennan
Journal:  Nucleic Acids Res       Date:  1987-09-11       Impact factor: 16.971

3.  Absolute configuration of the diastereomers of adenosine 5'-O-(1-thiotriphosphate): consequences for the stereochemistry of polymerization by DNA-dependent RNA polymerase from Escherichia coli.

Authors:  P M Burgers; F Eckstein
Journal:  Proc Natl Acad Sci U S A       Date:  1978-10       Impact factor: 11.205

4.  Structural basis for activation of alpha-boranophosphate nucleotide analogues targeting drug-resistant reverse transcriptase.

Authors:  P Meyer; B Schneider; S Sarfati; D Deville-Bonne; C Guerreiro; J Boretto; J Janin; M Véron; B Canard
Journal:  EMBO J       Date:  2000-07-17       Impact factor: 11.598

5.  Oxygen replacement with selenium at the thymidine 4-position for the Se base pairing and crystal structure studies.

Authors:  Jozef Salon; Jia Sheng; Jiansheng Jiang; Guexiong Chen; Julianne Caton-Williams; Zhen Huang
Journal:  J Am Chem Soc       Date:  2007-03-28       Impact factor: 15.419

6.  Difluoromethylenediphosphonate: a convenient, scalable, and high-yielding synthesis.

Authors:  Nicholas A Boyle
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

7.  Synthesis of acyclothymidine triphosphate and alpha-P-boranotriphosphate and their substrate properties with retroviral reverse transcriptase.

Authors:  Ping Li; Mikhail Dobrikov; Hongyan Liu; Barbara Ramsay Shaw
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

8.  Phenotypic mechanism of HIV-1 resistance to 3'-azido-3'-deoxythymidine (AZT): increased polymerization processivity and enhanced sensitivity to pyrophosphate of the mutant viral reverse transcriptase.

Authors:  D Arion; N Kaushik; S McCormick; G Borkow; M A Parniak
Journal:  Biochemistry       Date:  1998-11-10       Impact factor: 3.162

Review 9.  Analogs of diadenosine tetraphosphate (Ap4A).

Authors:  Andrzej Guranowski
Journal:  Acta Biochim Pol       Date:  2003       Impact factor: 2.149

10.  Convenient synthesis of nucleoside borane diphosphate analogues: deoxy- and ribonucleoside 5'-P(alpha)-boranodiphosphates.

Authors:  Ping Li; Barbara Ramsay Shaw
Journal:  J Org Chem       Date:  2004-10-15       Impact factor: 4.354
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  4 in total

1.  Synthesis, properties, and biological activity of boranophosphate analogs of the mRNA cap: versatile tools for manipulation of therapeutically relevant cap-dependent processes.

Authors:  Joanna Kowalska; Anna Wypijewska del Nogal; Zbigniew M Darzynkiewicz; Janina Buck; Corina Nicola; Andreas N Kuhn; Maciej Lukaszewicz; Joanna Zuberek; Malwina Strenkowska; Marcin Ziemniak; Maciej Maciejczyk; Elzbieta Bojarska; Robert E Rhoads; Edward Darzynkiewicz; Ugur Sahin; Jacek Jemielity
Journal:  Nucleic Acids Res       Date:  2014-08-22       Impact factor: 16.971

2.  Towards mRNA with superior translational activity: synthesis and properties of ARCA tetraphosphates with single phosphorothioate modifications.

Authors:  Malwina Strenkowska; Joanna Kowalska; Maciej Lukaszewicz; Joanna Zuberek; Wei Su; Robert E Rhoads; Edward Darzynkiewicz; Jacek Jemielity
Journal:  New J Chem       Date:  2010-01-01       Impact factor: 3.591

3.  New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors.

Authors:  Ivan B Yanachkov; Hung Chang; Milka I Yanachkova; Edward J Dix; Michelle A Berny-Lang; Thomas Gremmel; Alan D Michelson; George E Wright; Andrew L Frelinger
Journal:  Eur J Med Chem       Date:  2015-11-09       Impact factor: 6.514

4.  Synthesis, Hydrolysis, and Protonation-Promoted Intramolecular Reductive Breakdown of Potential NRTIs: Stavudine α-P-Borano-γ-P-N-L-tryptophanyltriphosphates.

Authors:  Zhihong Xu; Barbara Ramsay Shaw
Journal:  Molecules       Date:  2015-10-16       Impact factor: 4.411
  4 in total

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