Semisynthesis of 6-Chloropurine-2′-deoxyriboside 5′-Dimethoxytrityl 3′-(2-Cyanoethyl-N,N-diisopropylamino)Phosphoramidite and its Use in the Synthesis of Fluorescently Labeled Oligonucleotides

@article{Uddin2010SemisynthesisO6,
  title={Semisynthesis of 6-Chloropurine-2′-deoxyriboside 5′-Dimethoxytrityl 3′-(2-Cyanoethyl-N,N-diisopropylamino)Phosphoramidite and its Use in the Synthesis of Fluorescently Labeled Oligonucleotides},
  author={Md. Jashim Uddin and Michael I Schulte and Leena Maddukuri and Joel M. Harp and Lawrence J. Marnett},
  journal={Nucleosides, Nucleotides \& Nucleic Acids},
  year={2010},
  volume={29},
  pages={831 - 840}
}
An efficient enzymatic synthesis of 6-chloropurine-2′-deoxyriboside from the reaction of 6-chloropurine with 2′-deoxycytidine catalyzed by nucleoside-2′-deoxyribosyltransferase (E.C. 2.4.2.6) followed by chemical conversion into the 5′-dimethoxytrityl 3′-(2-cyanoethyl-N,N-diisopropylamino) phosphoramidite derivative is described. The phosphoramidite derivative was incorporated site-specifically into an oligonucleotide and used for the introduction of a tethered tetramethylrhodamine-cadaverine… 
View on Taylor & Francis
europepmc.org
2 Citations

2 Citations

Semisynthesis of 6-Chloropurine-2′-deoxyriboside 5′-Dimethoxytrityl 3′-(2-Cyanoethyl-N,N-diisopropylamino)phosphoramidite and Its Use in the Synthesis of Fluorescently Labeled Oligonucleotides.

The semisynthesis of (IV) consists of a combination of enzymatic and chemical synthesis providing significant advantages over chemical synthesis.

New trends in the biocatalytic production of nucleosidic active pharmaceutical ingredients using 2'-deoxyribosyltransferases.

References

SHOWING 1-10 OF 13 REFERENCES

Identification of the Active Site Nucleophile in Nucleoside 2-Deoxyribosyltransferase as Glutamic Acid 98 (*)

Chemical modification and mutagenesis studies have identified Glu-98 as the active site nucleophile of nucleoside 2-deoxyribosyltransferase and model studies on the base lability of peptides containing glutamyl esters suggested that the -carboxylate of GLU-98 was esterfied during catalysis.

Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells

Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as…

Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase

Trifluoroacetylation of 2′-deoxyinosine (2), obtained by enzymatic deamination of 2′-deoxyadenosine (1), gave the 3′,5′-bis-O-trifluoroacetate (3). Reaction of the electronegatively substituted deo...

Biocatalytic synthesis of base-modified 2′-deoxy-β-D-ribonucleosides with bacterial whole cells

Whole-cell syntheses of representative modified purine and pyrimidine 2′-deoxy-β-D-ribonucleosides are described. The transglycosylation reactions were carried out at 55¡C using the thermostable…

Site-specific synthesis of oligonucleotides containing malondialdehyde adducts of deoxyguanosine and deoxyadenosine via a postsynthetic modification strategy.

This work provides an alternative route to the M1dG adducted oligon nucleotide and, to date, the only viable strategy for the site-specific synthesis of OPdA-modified oligonucleotides that rely on a postsynthetic modification strategy.

Purine nucleoside synthesis, an efficient method employing nucleoside phosphorylases.

Of the substrates tested, the most potent stabilizers of Urd Pases, dThd Pase, and PN Pase were uridine, 2'-deoxyribose 1-phosphate, and ribose1-ph phosphate, respectively.

New Strategy for the Synthesis of Oligodeoxynucleotides Bearing Adducts at Exocyclic Amino Sites of Purine Nucleosides

Report a novel postoligomerization strategy that provides complete regiochemical and stereochemical control of adduction. In this method the natural polarity of reaction, i.e., with the heterocyclic…

Fluorescein-labeled oligonucleotides for real-time pcr: using the inherent quenching of deoxyguanosine nucleotides.

Real-time quantification and mutation detection with a simple single labeled probe is demonstrated by using the inherent quenching of deoxyguanosine nucleotides in the amplicon, complicated probe designs involving internal quenched can be avoided.

Fluorescent-oligonucleotide probing of whole cells for determinative, phylogenetic, and environmental studies in microbiology

Fluorescent-dye-conjugated oligonucleotides were used to classify 14 Fibrobacter strains by fluorescence microscopy and the direct detection of F. intestinalis in mouse cecum samples demonstrated the application of this technique to the characterization of complex natural samples.

Direct fluorescence analysis of genetic polymorphisms by hybridization with oligonucleotide arrays on glass supports.

The utility of the method was demonstrated in the parallel analysis of 5 point mutations from exon 4 of the human tyrosinase gene, as was the relative efficacy of hybridization with single or double-stranded PCR products.