Literature DB >> 17365797

Synthesis of 3',5'-cyclic diguanylic acid (cdiGMP) using 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl as a protecting group for 2'-hydroxy functions of ribonucleosides.

Hongbin Yan1, Aimé López Aguilar.   

Abstract

We herein report a convenient synthesis of 3',5'-cyclic diguanylic acid via the modified H-phosphonate approach. The 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) group was used as protecting group for the 2'-hydroxy functions of ribonucleosides. Complete unblocking of the fully protected 3',5'-cyclic diguanylic acid gave cdiGMP as a homogeneous compound in an excellent yield.

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Year:  2007        PMID: 17365797     DOI: 10.1080/15257770601112762

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


  7 in total

Review 1.  Rationale, progress and development of vaccines utilizing STING-activating cyclic dinucleotide adjuvants.

Authors:  Thomas W Dubensky; David B Kanne; Meredith L Leong
Journal:  Ther Adv Vaccines       Date:  2013-11

2.  An Improved Strategy for the Chemical Synthesis of 3',5'-Cyclic Diguanylic Acid.

Authors:  Andrzej Grajkowski; Mayumi Takahashi; Tomasz Kaczyński; Suresh C Srivastava; Serge L Beaucage
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2019-04-10

3.  One-flask syntheses of c-di-GMP and the [Rp,Rp] and [Rp,Sp] thiophosphate analogues.

Authors:  Barbara L Gaffney; Elizabeth Veliath; Jianwei Zhao; Roger A Jones
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

4.  One-flask synthesis of cyclic diguanosine monophosphate (c-di-GMP).

Authors:  Barbara L Gaffney; Roger A Jones
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2012-03

5.  Convenient synthesis of a propargylated cyclic (3'-5') diguanylic acid and its "click" conjugation to a biotinylated azide.

Authors:  Andrzej Grajkowski; Jacek Cieślak; Alexei Gapeev; Christian Schindler; Serge L Beaucage
Journal:  Bioconjug Chem       Date:  2010-10-13       Impact factor: 4.774

Review 6.  The bacterial second messenger c-di-GMP: probing interactions with protein and RNA binding partners using cyclic dinucleotide analogs.

Authors:  Carly A Shanahan; Scott A Strobel
Journal:  Org Biomol Chem       Date:  2012-10-29       Impact factor: 3.876

7.  2'-Fluoro-c-di-GMP as an oral vaccine adjuvant.

Authors:  Jia Li; Rhonda Kuo Lee; Wangxue Chen; Hongbin Yan
Journal:  RSC Adv       Date:  2019-12-16       Impact factor: 4.036

  7 in total

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