Synthesis of the 5′-Se-Thymidine Phosphoramidite and Convenient Labeling of DNA Oligonucleotide

Huang, Zhen

doi:10.1021/ol200397c

Cited by 14 publications

(7 citation statements)

References 30 publications

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“…Next, Tau-dTDP β-phosphoramidate 33 was prepared according to the DCC-mediated phosphoramidate coupling between taurine and the triethylammonium salt of thymidine diphosphate 32. Compound 32 was derived in turn from 5′-Otosyl derivative 31, 16 upon treatment with tris(tetra-n-butylammonium) hydrogen pyrophosphate, acting as a nucleophile to displace the tosyl group as reported by Davisson et al 17 (Scheme 6).…”

Section: Resultsmentioning

confidence: 97%

Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

Groaz

Margamuljana

et al. 2015

Org. Biomol. Chem.

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Novel unnatural 5'-phosphoramidate nucleosides, capable of being processed as substrates by DNA polymerases for multiple nucleotide incorporations, have been designed. The mimics feature metabolites such as taurine and a broad range of aliphatic sulfonates coupled through a P-N bond to the 5'-phosphate position of deoxynucleotides, to allow binding interactions in the enzyme active site. The utility of all of the analogues as pyrophosphate mimics was demonstrated for the chain elongation of DNA, using both thermophilic and mesophilic microbial polymerases.

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Section: Resultsmentioning

confidence: 97%

Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

Groaz

Margamuljana

et al. 2015

Org. Biomol. Chem.

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“…69 There are also some reports about the anticancer activity of selenium-containing compounds, including seleniummodified nucleotides. 67,[70][71][72] In our laboratory, many seleniumcontaining nucleosides, nucleotides and nucleic acids have been synthesized. Considering the possible therapeutic activity of the selenium compounds, these nucleosides, nucleotides and nucleic acids have been screened and shown promising anticancer and antimicrobial activities.…”

Section: Perspective Of Selenium Derivatization Of Nucleic Acidsmentioning

confidence: 99%

Nucleic acid X-ray crystallography via direct selenium derivatization

2011

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X-ray crystallography has proven to be an essential tool for structural studies of bio-macromolecules at the atomic level. There are two major bottle-neck problems in the macromolecular crystal structure determination: phasing and crystallization. Although the selenium derivatization is routinely used for solving novel protein structures through the MAD phasing technique, the phase problem is still a critical issue in nucleic acid crystallography. The background and current progress of using direct selenium-derivatization of nucleic acids (SeNA) to solve the phase problem and to facilitate nucleic acid crystallization for X-ray crystallography are summarized in this tutorial review.

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“…56 Contrary to the afore cited Sonogashira cross-couplings and the oxidative acetylenic homocoupling, this method is performed on deprotected DNA, already cleaved from solid support. These studies demonstrate the progress achieved in convenient synthesis of modified oligonucleotides, and further elaboration is encouraged; nevertheless, there is a growing demand 40 in developing advanced approaches, in particular for RNA on a postsynthetic level that is described less extensively than for DNA.…”

Section: ■ Introductionmentioning

confidence: 86%

Postsynthetic on Column RNA Labeling via Stille Coupling

Wicke

Engels

2012

Bioconjugate Chem.

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Stille Coupling is a versatile C-C bond forming reaction with high functional group tolerance under mild conditions. Our on column synthesis concept for RNA modification is based on the incorporation of iodo substituted nucleotide precursors to RNA during automated standard solid phase synthesis via TBDMS-, TC-, and ACE- protecting group strategies. Subsequently, the RNA, still bound on solid support, is ready for orthogonal postsynthetic functionalization via Stille cross-couplings utilizing the advantages of solid phase synthesis. Several monomer test reactions were employed with 2-iodo adenosine and 5-iodo uridine and organostannanes as coupling partners under different conditions, changing the catalyst/ligand system, temperature, and reaction time as well as conventional heating and microwave irradiation. Finally, Stille cross-couplings under optimized conditions were transferred to fully protected 5-mer and 12-mer RNA oligonucleotides on-column. Deprotection and cleavage from solid support resulted in site-specifically labeled oligonucleotides. Derivatizations via Stille cross-couplings were performed initially with vinyltributylstannane as well as later with 2-furanyl-, 2-thiophene-, and benzothiophene-2-tributylstannanes yielding fluorescently functionalized RNA.

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Synthesis of the 5′-Se-Thymidine Phosphoramidite and Convenient Labeling of DNA Oligonucleotide

Cited by 14 publications

References 30 publications

Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

Nucleic acid X-ray crystallography via direct selenium derivatization

Postsynthetic on Column RNA Labeling via Stille Coupling

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