Literature DB >> 22966945

Preparation of synthetically challenging nucleotides using cyanoethyl P-imidazolides and microwaves.

Malwina Strenkowska1, Przemyslaw Wanat, Marcin Ziemniak, Jacek Jemielity, Joanna Kowalska.   

Abstract

We describe a general method for the elongation of nucleoside oligophosphate chains by means of cyanoethyl (CE) phosphorimidazolides. Though the method requires a phosphorylation and subsequent deprotection reaction, both steps could be achieved in one pot without isolation/purification of the initial phosphorylation product. We have also found that pyrophosphate bond formation by this method is significantly accelerated by microwave irradiation.

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Year:  2012        PMID: 22966945     DOI: 10.1021/ol302071f

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


  12 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.  Chemical pyrophosphorylation of functionally diverse peptides.

Authors:  Alan M Marmelstein; Lisa M Yates; John H Conway; Dorothea Fiedler
Journal:  J Am Chem Soc       Date:  2013-12-26       Impact factor: 15.419

Review 3.  Beyond Triphosphates: Reagents and Methods for Chemical Oligophosphorylation.

Authors:  Scott M Shepard; Henning J Jessen; Christopher C Cummins
Journal:  J Am Chem Soc       Date:  2022-04-26       Impact factor: 16.383

4.  Nucleoside Tetra- and Pentaphosphates Prepared Using a Tetraphosphorylation Reagent Are Potent Inhibitors of Ribonuclease A.

Authors:  Scott M Shepard; Ian W Windsor; Ronald T Raines; Christopher C Cummins
Journal:  J Am Chem Soc       Date:  2019-11-11       Impact factor: 15.419

5.  Corroboration of Zn(ii)-Mg(ii)-tertiary structure interplays essential for the optimal catalysis of a phosphorothiolate thiolesterase ribozyme.

Authors:  Tzu-Pin Wang; Yu-Chih Su; Yi Chen; Scott Severance; Chi-Ching Hwang; Yi-Ming Liou; Chia-Hui Lu; Kun-Liang Lin; Rui Jing Zhu; Eng-Chi Wang
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361

6.  A procedure for the preparation and isolation of nucleoside-5'-diphosphates.

Authors:  Heidi J Korhonen; Hannah L Bolt; David R W Hodgson
Journal:  Beilstein J Org Chem       Date:  2015-04-10       Impact factor: 2.883

7.  Cap analogs modified with 1,2-dithiodiphosphate moiety protect mRNA from decapping and enhance its translational potential.

Authors:  Malwina Strenkowska; Renata Grzela; Maciej Majewski; Katarzyna Wnek; Joanna Kowalska; Maciej Lukaszewicz; Joanna Zuberek; Edward Darzynkiewicz; Andreas N Kuhn; Ugur Sahin; Jacek Jemielity
Journal:  Nucleic Acids Res       Date:  2016-10-07       Impact factor: 16.971

8.  Analysis of mononucleotides by tandem mass spectrometry: investigation of fragmentation pathways for phosphate- and ribose-modified nucleotide analogues.

Authors:  Dominika Strzelecka; Sebastian Chmielinski; Sylwia Bednarek; Jacek Jemielity; Joanna Kowalska
Journal:  Sci Rep       Date:  2017-08-21       Impact factor: 4.379

Review 9.  Applications of Phosphate Modification and Labeling to Study (m)RNA Caps.

Authors:  Marcin Warminski; Pawel J Sikorski; Joanna Kowalska; Jacek Jemielity
Journal:  Top Curr Chem (Cham)       Date:  2017-01-23

10.  Two-headed tetraphosphate cap analogs are inhibitors of the Dcp1/2 RNA decapping complex.

Authors:  Marcin Ziemniak; Jeffrey S Mugridge; Joanna Kowalska; Robert E Rhoads; John D Gross; Jacek Jemielity
Journal:  RNA       Date:  2016-01-29       Impact factor: 4.942

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