Literature DB >> 16787069

Synthesis of mixed sequence borane phosphonate DNA.

Heather Brummel McCuen1, Mary S Noé, Agnieszka B Sierzchala, Adrian P Higson, Marvin H Caruthers.   

Abstract

A novel solid-phase phosphoramidite-based method has been developed for the synthesis of borane phosphonate DNA. Keys to this new approach are replacement of the common 5'-dimethoxytrityl blocking group with a 5'-silyl ether and the use of new protecting groups on the bases (adenine, N6-dimethoxytrityl; cytosine, N4-trimethoxytrityl; guanine, N2-[9-fluorenylmethoxycarbonyl]; thymine, N3-anisoyl). Because of these developments, it is now possible for the first time to synthesize oligodeoxynucleotides having any combination of the four 2'-deoxynucleosides and both phosphate and borane phosphonate internucleotide linkages (including oligomers having exclusively borane phosphonate linkages).

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Year:  2006        PMID: 16787069     DOI: 10.1021/ja061757e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

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

Authors:  Qianwei Han; Stefan G Sarafianos; Eddy Arnold; Michael A Parniak; Barbara L Gaffney; Roger A Jones
Journal:  Tetrahedron       Date:  2009-09-19       Impact factor: 2.457

Review 2.  Synthesis of DNA/RNA and their analogs via phosphoramidite and H-phosphonate chemistries.

Authors:  Subhadeep Roy; Marvin Caruthers
Journal:  Molecules       Date:  2013-11-18       Impact factor: 4.411

3.  Solid-Phase Synthesis of Boranophosphate/Phosphorothioate/Phosphate Chimeric Oligonucleotides and Their Potential as Antisense Oligonucleotides.

Authors:  Yuhei Takahashi; Kazuki Sato; Takeshi Wada
Journal:  J Org Chem       Date:  2021-12-15       Impact factor: 4.354

  3 in total

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