Advanced search
1 file | 499.13 KB

Fast RNA conjugations on solid phase by strain-promoted cycloadditions

(2012) ORGANIC & BIOMOLECULAR CHEMISTRY. 10(33). p.6633-6639
Author
Organization
Abstract
Strain promoted cycloaddition is presented as a tool for RNA conjugation on the solid phase; RNA-cyclooctyne conjugates are prepared by cycloaddition to both azide (strain-promoted azide-alkyne cycloaddition, SPAAC) and nitrile oxide dipoles (strain-promoted nitrile oxide-alkyne cycloaddition, SPNOAC). The conjugation is compatible with 2'-OMe blocks and with 2'-O-TBDMS protection on the ribose moieties of the sugar. Nitrile oxide dipoles are found to be more reactive click partners than azides. The conjugation proceeds within 10 min in aqueous solvents, at room temperature without any metal catalyst and tolerates dipoles of varying steric bulk and electronic demands, including pyrenyl, coumarin and dabcyl derivatives.
Keywords
FUNCTIONALIZATION, DNA, EFFICIENT SYNTHESIS, 3-DIPOLAR CYCLOADDITION, 1, AZIDE-ALKYNE CYCLOADDITION, FREE CLICK CHEMISTRY, POLYMER, LIGATION

Downloads

  • (...).pdf
    • full text
    • |
    • UGent only
    • |
    • PDF
    • |
    • 499.13 KB

Citation

Please use this url to cite or link to this publication:

Chicago
Singh, Ishwar, Colin Freeman, Annemieke Madder, Joseph S Vyle, and Frances Heaney. 2012. “Fast RNA Conjugations on Solid Phase by Strain-promoted Cycloadditions.” Organic & Biomolecular Chemistry 10 (33): 6633–6639.
APA
Singh, I., Freeman, C., Madder, A., Vyle, J. S., & Heaney, F. (2012). Fast RNA conjugations on solid phase by strain-promoted cycloadditions. ORGANIC & BIOMOLECULAR CHEMISTRY, 10(33), 6633–6639.
Vancouver
1.
Singh I, Freeman C, Madder A, Vyle JS, Heaney F. Fast RNA conjugations on solid phase by strain-promoted cycloadditions. ORGANIC & BIOMOLECULAR CHEMISTRY. 2012;10(33):6633–9.
MLA
Singh, Ishwar, Colin Freeman, Annemieke Madder, et al. “Fast RNA Conjugations on Solid Phase by Strain-promoted Cycloadditions.” ORGANIC & BIOMOLECULAR CHEMISTRY 10.33 (2012): 6633–6639. Print.
@article{4350588,
  abstract     = {Strain promoted cycloaddition is presented as a tool for RNA conjugation on the solid phase; RNA-cyclooctyne conjugates are prepared by cycloaddition to both azide (strain-promoted azide-alkyne cycloaddition, SPAAC) and nitrile oxide dipoles (strain-promoted nitrile oxide-alkyne cycloaddition, SPNOAC). The conjugation is compatible with 2'-OMe blocks and with 2'-O-TBDMS protection on the ribose moieties of the sugar. Nitrile oxide dipoles are found to be more reactive click partners than azides. The conjugation proceeds within 10 min in aqueous solvents, at room temperature without any metal catalyst and tolerates dipoles of varying steric bulk and electronic demands, including pyrenyl, coumarin and dabcyl derivatives.},
  author       = {Singh, Ishwar and Freeman, Colin and Madder, Annemieke and Vyle, Joseph S and Heaney, Frances},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  language     = {eng},
  number       = {33},
  pages        = {6633--6639},
  title        = {Fast RNA conjugations on solid phase by strain-promoted cycloadditions},
  url          = {http://dx.doi.org/10.1039/c2ob25628b},
  volume       = {10},
  year         = {2012},
}

Altmetric
View in Altmetric
Web of Science
Times cited: