Literature DB >> 22147418

Synthesis of the tellurium-derivatized phosphoramidites and their incorporation into DNA oligonucleotides.

Sibo Jiang1, Jia Sheng, Zhen Huang.   

Abstract

In this unit, an efficient method for the synthesis of 2'-tellerium-modified phosphoramidite and its incorporation into oligonucleotide are presented. We choose 5'-O-DMTr-2,2'-anhydro-uridine and -thymidine nucleosides (S.1, S.2) as starting materials due to their easy preparation. The 5'-O-DMTr-2,2'-anhydro-uridine and -thymidine can be converted to the corresponding 2'-tellerium-derivatized nucleosides by treating with the telluride nucleophiles. Subsequently, the 2'-Te-nucleosides can be transformed into 3'-phosphoramidites, which are the building blocks for DNA/RNA synthesis. The DNA synthesis, purification, and applications of oligonucleotides containing 2'-Te-U or 2'-Te-T are described in the protocol.
© 2011 by John Wiley & Sons, Inc.

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Year:  2011        PMID: 22147418      PMCID: PMC4618196          DOI: 10.1002/0471142700.nc0125s47

Source DB:  PubMed          Journal:  Curr Protoc Nucleic Acid Chem        ISSN: 1934-9270


  34 in total

1.  Synthesis of a 2'-Se-thymidine phosphoramidite and its incorporation into oligonucleotides for crystal structure study.

Authors:  Jia Sheng; Jiansheng Jiang; Jozef Salon; Zhen Huang
Journal:  Org Lett       Date:  2007-01-31       Impact factor: 6.005

2.  Crystal structure and mechanism of a DNA (6-4) photolyase.

Authors:  Melanie J Maul; Thomas R M Barends; Andreas F Glas; Max J Cryle; Tatiana Domratcheva; Sabine Schneider; Ilme Schlichting; Thomas Carell
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Bio-incorporation of telluromethionine into buried residues of dihydrofolate reductase.

Authors:  J O Boles; K Lewinski; M Kunkle; J D Odom; B Dunlap; L Lebioda; M Hatada
Journal:  Nat Struct Biol       Date:  1994-05

Review 4.  Chalcogen-analogs of amino acids. Their use in X-ray crystallographic and folding studies of peptides and proteins.

Authors:  D Besse; N Budisa; W Karnbrock; C Minks; H J Musiol; S Pegoraro; F Siedler; E Weyher; L Moroder
Journal:  Biol Chem       Date:  1997 Mar-Apr       Impact factor: 3.915

5.  Synthesis of the 5'-Se-thymidine phosphoramidite and convenient labeling of DNA oligonucleotide.

Authors:  Wen Zhang; Zhen Huang
Journal:  Org Lett       Date:  2011-03-24       Impact factor: 6.005

6.  Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide.

Authors:  Jonathan K Watts; Blair D Johnston; Kumarasamy Jayakanthan; Alexander S Wahba; B Mario Pinto; Masad J Damha
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

7.  High-level biosynthetic substitution of methionine in proteins by its analogs 2-aminohexanoic acid, selenomethionine, telluromethionine and ethionine in Escherichia coli.

Authors:  N Budisa; B Steipe; P Demange; C Eckerskorn; J Kellermann; R Huber
Journal:  Eur J Biochem       Date:  1995-06-01

8.  Synthesis and crystallographic analysis of 5-Se-thymidine DNAs.

Authors:  Abdalla E A Hassan; Jia Sheng; Jiansheng Jiang; Wen Zhang; Zhen Huang
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

9.  First synthesis of 4'-selenonucleosides showing unusual Southern conformation.

Authors:  Lak Shin Jeong; Dilip K Tosh; Hea Ok Kim; Ting Wang; Xiyan Hou; Ho Seop Yun; Youngjoo Kwon; Sang Kook Lee; Jungwon Choi; Long Xuan Zhao
Journal:  Org Lett       Date:  2007-12-19       Impact factor: 6.005

10.  Selenomethionyl proteins produced for analysis by multiwavelength anomalous diffraction (MAD): a vehicle for direct determination of three-dimensional structure.

Authors:  W A Hendrickson; J R Horton; D M LeMaster
Journal:  EMBO J       Date:  1990-05       Impact factor: 11.598

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