Literature DB >> 15043142

Functionalization of guanosine and 2'-deoxyguanosine at C6: a modified Appel process and S(N)Ar displacement of imidazole.

Zlatko Janeba1, Xiaoyu Lin, Morris J Robins.   

Abstract

Treatment of sugar-protected 2-N-trityl derivatives of guanosine and 2'-deoxyguanosine with imidazole/triphenylphosphine/iodine/ethyldiisopropylamine gives the corresponding 6-(imidazol-1-yl)-2-(tritylamino)purine nucleosides. S(N)Ar displacement of the imidazole moiety with nucleophiles provides 2-amino-6-substituted-purine nucleosides and 2'-deoxynucleosides.

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Year:  2004        PMID： 15043142     DOI： 10.1081/ncn-120027823

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN： 1525-7770            Impact factor:   1.381


  7 in total

1.  Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers via intermediate O6-(benzotriazol-1-yl) derivatives.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2012-06

2.  One-pot etherification of purine nucleosides and pyrimidines.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  Facile Modifications at the C4 Position of Pyrimidine Nucleosides via In Situ Amide Activation with 1H-Benzotriazol-1-yloxy-tris(dimethyl-amino)phosphonium Hexafluorophosphate.

Authors:  Hari K Akula; Mahesh K Lakshman
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2019-01-28

4.  A simple method for C-6 modification of guanine nucleosides.

Authors:  Mahesh K Lakshman; Josh Frank
Journal:  Org Biomol Chem       Date:  2009-06-01       Impact factor: 3.876

5.  Synthesis of N6 ,N6-Dialkyl Adenine Nucleosides With In Situ Formed Hexaalkylphosphorus Triamides.

Authors:  Mahesh K Lakshman; Asad Choudhury; Suyeal Bae; Eliezer Rochttis; Padmanava Pradhan; Amit Kumar
Journal:  European J Org Chem       Date:  2009-01-01

6.  Simple Synthesis of Amides and Weinreb Amides via Use of PPh3 or Polymer-Supported PPh3 and Iodine.

Authors:  Amit Kumar; Hari Kiran Akula; Mahesh K Lakshman
Journal:  European J Org Chem       Date:  2010-05

7.  MutT homologue 1 (MTH1) catalyzes the hydrolysis of mutagenic O6-methyl-dGTP.

Authors:  Ann-Sofie Jemth; Robert Gustafsson; Lars Bräutigam; Linda Henriksson; Karl S A Vallin; Antonio Sarno; Ingrid Almlöf; Evert Homan; Azita Rasti; Ulrika Warpman Berglund; Pål Stenmark; Thomas Helleday
Journal:  Nucleic Acids Res       Date:  2018-11-16       Impact factor: 16.971
  7 in total

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