Aldehyde Modification

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Applicable Products

2056 Formylindole-Modifier-CE Phosphoramidite

Physical & Dilution Data

Dilution volumes (in ml) are for 0.1M solutions in dry acetonitrile (4050). Adjust accordingly for other concentrations. For µmol pack sizes, dilute as 100µmol/ml to achieve 0.1M.

Item

Mol. Formula

Mol. Wt.

Unit Wt.

250mg

500mg

1g

2056 C44H50N3O7P 763.87 323.24 3.27 6.55 13.09

Coupling

An extended coupling time of 15min is recommended.

Cleavage & Deprotection

Deprotection is dictated by other modifiers and nucleobase protection. This is stable to all commonly used deprotection strategies.

Storage & Stability

Stable in solutions for up to 4 days; store at -20oC.

Example conjugation using 2056 with a functionalised hydrazine1

  1. Synthesise the 5’- or mid-sequence aldehyde-modified oligo as per notes above. Retain on the support.
  2. Prepare a solution of the reagents used for the conjugation (10mM N,N-diphenylhydrazine hydrochloride and 10mM sodium acetate in 1.5ml ethanol).
  3. To the solution add the support-bound oligo (ca. 0.5μmol) then shake at 60°C for 24h. Alternatively the solution from Step 2 can be passed through the column using two syringes.
  4. Evaporate the solution under vacuum, or (if using syringes), remove the solution from the column and wash the resin in the column with MeCN. Dry the resin by passing argon through the column.
  5. The conjugate can then be deprotected and cleaved from the solid support using deprotection conditions suitable for the modified oligo.
  6. Pass through a G25 column to remove the deprotection solution.
  7. The modified oligo is now ready for purification.

Further examples of the use of an alternative aldehyde modifier2 (whose protocols could be extended to 2056) are available in the literature.

References

  1. A facile incorporation of the aldehyde function into DNA: 3-formylindole nucleoside as an aldehyde containing universal nucleoside, A. Okamoto, K.Tainaka and I. Saito, Tetrahedron Lett., 43, 4581-4583, 2002.
  2. Synthesis of peptide-oligonucleotide conjugates with single and multiple peptides attached to 2’-aldehydes through thiazolidine, oxime, and hydrazine linkages, T.S. Zatsepin, D.A. Stetsenko, A.A. Arzumanov, E.A. Romanova, M.J. Gait and T.S. Oretskaya, Bioconjugate Chemistry, 13, 822-830, 2002.
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