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Fmoc-Amino Modifier C6-dT CE-Phosphoramidite

Fmoc-Amino Modifier C6-dT CE-Phosphoramidite

Phosphoramidite for incorporation of a nucleobase-tethered amine that can be deprotected prior to cleaving the oligonucleotide from the solid support.
  • Incorporates primary amine internally to an oligonucleotide, for subsequent conjugation.
  • Base labile Fmoc group useful where purifcation "handle" is not necessary.
  • After deprotection, the primary amine is distanced from the oligonucleotide by a total of 10 atoms and can be labelled or attached to a biomolecule such as an enzyme.
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Product information

The (fluorenylmethyl)carbamoyl (Fmoc) group has been shown to be a useful amine protecting group for amine modification of oligonucleotides.(1) It is removed during cleavage/deprotection with ammonium hydroxide. Alternatively, the Fmoc group can be removed before cleavage of the oligonucleotide from the solid support,(2) e.g., with piperidine, simplifying the acylation process. After the acylation is complete, the labeled oligonucleotide can then be cleaved from the support and further deprotected with ammonium hydroxide.
For applications requiring a nucleobase-tethered amine at internal or 5' positions, we offer this Fmoc-protected compound Fmoc-Amino-Modifier-C6-dT CE-Phosphoramidite (BA0287), which offers the possibility of on-bead acylation as discussed above. It is an alternative to the venerable Amino-Modifier-C6-dT CE-Phosphoramidite (BA0015 / LK2135) which bears a trifluoroacetyl (TFA) protecting group. The TFA group cannot be removed without cleavage of the oligonucleotide from the resin.

For 3'-amino-modification involving Fmoc-deprotection, see BA0299 and BA0307, and LK2350.

Ref:

  1. Nelson, P. S.; Kent, M.; Muthini, S. Nucl. Acids Res. 1992, 20, 6253-6259.
  2. For example, see: (a) Gartner, Z. J.; Kanan, M. W.; Liu, D. R. J. Am. Chem. Soc. 2002, 124, 10304-10306; see Supporting Information, p. 3. (b) Gartner, Z. J.; Tse, B. N.; Grubina, R.; Doyon, J. B.; Snyder, T. M.; Liu, D. R. Science 2004, 305, 1601-1605; see Supporting Online Material, p. 2.

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