Literature DB >> 21256007

Improved synthesis of 5-hydroxymethyl-2'-deoxycytidine phosphoramidite using a 2'-deoxyuridine to 2'-deoxycytidine conversion without temporary protecting groups.

Anders S Hansen1, Armin Thalhammer, Afaf H El-Sagheer, Tom Brown, Christopher J Schofield.   

Abstract

5-Hydroxymethylcytosine has recently been characterized as the 'sixth base' in human DNA. To enable research on this DNA modification, we report an improved method for the synthesis of 5-hydroxymethyl-2'-deoxycytidine ((5-HOMe)dC) phosphoramidite for site-specific incorporation into oligonucleotides. To minimize manipulations we employed a temporary protecting group-free 2'-deoxyuridine to 2'-deoxycytidine conversion procedure that utilizes phase transfer catalysis. The desired (5-HOMe)dC phosphoramidite is obtained in six steps and 24% overall yield from 2'-deoxyuridine.
Copyright © 2011 Elsevier Ltd. All rights reserved.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 21256007     DOI： 10.1016/j.bmcl.2010.12.098

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  8 in total

1.  Preparation of DNA containing 5-hydroxymethyl-2'-deoxycytidine modification through phosphoramidites with TBDMS as 5-hydroxymethyl protecting group.

Authors:  Qing Dai; Chuan He
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2011-12

2.  Intermolecular 'cross-torque': the N4-cytosine propargyl residue is rotated to the 'CH'-edge as a result of Watson-Crick interaction.

Authors:  Olwen Domingo; Isabell Hellmuth; Andres Jäschke; Christoph Kreutz; Mark Helm
Journal:  Nucleic Acids Res       Date:  2015-04-30       Impact factor: 16.971

3.  Syntheses of two 5-hydroxymethyl-2'-deoxycytidine phosphoramidites with TBDMS as the 5-hydroxymethyl protecting group and their incorporation into DNA.

Authors:  Qing Dai; Chun-Xiao Song; Tao Pan; Chuan He
Journal:  J Org Chem       Date:  2011-04-14       Impact factor: 4.354

4.  Synthesis of 5-Hydroxymethylcytidine- and 5-Hydroxymethyl-uridine-Modified RNA.

Authors:  Christian Riml; Ronald Micura
Journal:  Synthesis (Stuttg)       Date:  2016-04       Impact factor: 3.157

5.  An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2'-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate.

Authors:  Dong-Zhao Yang; Zhen-Zhen Chen; Mei Chi; Ying-Ying Dong; Shou-Zhi Pu; Qi Sun
Journal:  Molecules       Date:  2022-01-24       Impact factor: 4.411

6.  Synthesis and properties of DNA oligomers containing stereopure phosphorothioate linkages and C-5 modified deoxyuridine derivatives.

Authors:  Rintaro Iwata Hara; Reijiro Yoshino; Yohei Nukaga; Yusuke Maeda; Kazuki Sato; Takeshi Wada
Journal:  RSC Adv       Date:  2020-09-15       Impact factor: 4.036

7.  In-Gene Quantification of O(6)-Methylguanine with Elongated Nucleoside Analogues on Gold Nanoprobes.

Authors:  Ioannis A Trantakis; Arman Nilforoushan; Heidi A Dahlmann; Celine K Stäuble; Shana J Sturla
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

8.  Identification and biosynthesis of thymidine hypermodifications in the genomic DNA of widespread bacterial viruses.

Authors:  Yan-Jiun Lee; Nan Dai; Shannon E Walsh; Stephanie Müller; Morgan E Fraser; Kathryn M Kauffman; Chudi Guan; Ivan R Corrêa; Peter R Weigele
Journal:  Proc Natl Acad Sci U S A       Date:  2018-03-19       Impact factor: 11.205
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.