Polymer support oligonucleotide synthesis-XV

Köster, Hubert; Biernat, J.; McManus, J. F. A.; Wolter, Andreas; Stumpe, A.; Narang, Ch.K.; Sinha, N. D.

doi:10.1016/0040-4020(84)85108-x

Cited by 50 publications

(6 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Next, we examined the O-selective internucleotidic bond formation under solid-phase conditions according to a manual operation shown in Scheme . Although CPG resins have been generally used in the synthesis of oligodeoxynucleosides by use of DNA synthesizers, we selected commercially available highly cross-linked polystyrene (HCP) resins since the coupling on the HCP resin was very high and most suitable for the manual operation in our previous studies. In Scheme , the final deprotection and release of oligomers from the HCP resin were performed by treatment with concentrated NH 3 aq for 12 h because it took more prolonged time for removal of the cyanoethyl groups from the phosphoramidate residues formed on the nucleobases than those present in the internucleotidic phosphate (O−P(V)) bonds.…”

Section: Resultsmentioning

confidence: 99%

O-Selectivity and Utility of Phosphorylation Mediated by Phosphite Triester Intermediates in the N-Unprotected Phosphoramidite Method

et al. 2004

View full text Add to dashboard Cite

Previously, O-selective phosphorylation on polymer supports in the N-unprotected phosphoramidite method could not be carried out because the amino groups of dA and dC have high reactivity toward tervalent phosphorus(III)-type phosphitylating reagents. In this paper, we developed a new coupling strategy named the "activated phosphite method" in which the phosphitylation is mediated by phosphite triester intermediates 1. Application of 1-hydroxybenzotriazole as the promoter to the solid-phase synthesis resulted in excellent O-selectivity of more than 99.7%. This O-selectivity was explained by the frontier molecular orbital interactions between the reactive intermediates and the nucleophiles such as the amino or hydroxyl groups of nucleosides. Furthermore, longer oligonucleotides were synthesized not only by a manual operation but also by a DNA synthesizer. The utility of our new method was demonstrated by the successful synthesis of a base-labile modified oligodeoxyribonucleotide having 4-N-acetyldeoxycytidine residues. Finally, DNA 20-mers containing dA or dC could be synthesized in good yields by use of a combined reagent of 6-trifluoromethyl-1-hydroxybenzotriazole and benzimidazolium triflate.

show abstract

Section: Resultsmentioning

confidence: 99%

O-Selectivity and Utility of Phosphorylation Mediated by Phosphite Triester Intermediates in the N-Unprotected Phosphoramidite Method

et al. 2004

View full text Add to dashboard Cite

show abstract

“…In general, synthesis is performed on a solid support such as polystyrene,1° polya~rylarnide,~'-~~ cellulose,1P16 or controlled pore glass. 17,31, 32 The 3'-hydroxyl group of the nucleoside constituting the 3'-end of the DNA fragment to be synthesized usually serves as the point of attachment to the support. This strategy simplifies purification enormously by allowing excess reagents, side products, and solvents to simply be washed from the filtered support.…”

Section: A Phosphotriester Methodsmentioning

confidence: 99%

DNA synthesis and applications to molecular biology

Adams

Galluppi

1986

Medicinal Research Reviews

View full text Add to dashboard Cite

“…The commonly used CPG supports are equipped with 3-aminopropyl or the so called 'long chain aminoalkyl' groups (17,23). We have tried to modify them by introducing methacrylic acid residues.…”

Section: Nucleic Acids Researchmentioning

confidence: 99%

Universal solid supports for the synthesis of oligonucleotides with terminal 3′-phosphates

Markiewicz

Wyrzykiewicz

1989

Nucl Acids Res

View full text Add to dashboard Cite

The preparation of two types of supports based on controlled pore glass (CPG) is presented. These supports are compatible with established phosphoroamidite chemistry of oligonucleotides synthesis giving rise to an oligonucleotide with terminal 3'-phosphate function during final deprotection. CPG was modified with: (i) methacrylic acid derivatives and 2-mercaptoethanol (1) or (ii) aminoalkylsilane, succinic anhydride and benzidine (2). Support 2 can be also used for the synthesis of partially protected oligonucleotide 3'-phosphates.

show abstract

Polymer support oligonucleotide synthesis-XV

Cited by 50 publications

References 57 publications

O-Selectivity and Utility of Phosphorylation Mediated by Phosphite Triester Intermediates in the N-Unprotected Phosphoramidite Method

O-Selectivity and Utility of Phosphorylation Mediated by Phosphite Triester Intermediates in the N-Unprotected Phosphoramidite Method

DNA synthesis and applications to molecular biology

Universal solid supports for the synthesis of oligonucleotides with terminal 3′-phosphates

Contact Info

Product

Resources

About