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2'-fluoroarabinoside-Base (FANA-N)

2'-F-ANA-Bases

Code : [FANA-N]

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picture of 2'-fluoroarabinoside-Base (FANA-N)

Modification : 2'-F-ANA-Bases

Catalog Reference Number
Category
Modification Code
5 Prime
3 Prime
Internal
Molecular Weight (mw)
Extinction Coeficient (ec)
Technical Info (pdf)
Absorbance MAX
Emission MAX
Absorbance EC



27-6605N
Antisense
[FANA-N]
Y
Y
Y
323.43
11.075
27-6605N.pdf
-
-
-


Catalog NoScalePrice
27-6605N-0550 nmol$286.00
27-6605N-02200 nmol$286.00
27-6605N-011 umol$319.00
27-6605N-032 umol$410.00
27-6605N-065 umol$1,435.50
27-6605N-1010 umol$659.00
27-6605N-1515 umol$810.00
Discounts are available for 2'-F-ANA-Bases!
Modification* Discount Price Structure
1 site/order List price
2 sites/order 10% discount
3 sites/order 20% discount
4 sites/order 30% discount
5-9 sites/order 50% discount
10+ sites/order 60% discount
*Exceptions apply

Antisense Oligos (ODN) & siRNA Oligo Modifications

Click here for more information on antisense modifications, design & applications.

Arabinonucleosides are epimers of ribonucleosides with the chiral switch being at the 2' position of the sugar residue. 2'-F-ANA adopts a more DNA-like B-type helix conformation, not through the typical C2-endo conformation but, rather, through an unusual O4'-endo (east) pucker. However, the presence of the electronegative fluorine leads to a still significant increase (DTm1.2oC/mod) in melting temperature per modification (1). 2'-F-ANA-containing oligonucleotides exhibit very high binding specificity to their targets. Indeed, a single mismatch in a 2'-F-ANA-RNA duplex leads to a DTm of -7.2oC and in a 2'-F-ANA - DNA duplex a DTm of -3.9oC (2).

The presence of fluorine at the 2' position in 2' F-ANA leads to increased stability to hydrolysis under basic conditions relative to RNA and even 2'-F-RNA (1,3). The stability of 2'-F-ANA to nucleases also makes this a useful modification for enhancing the stability of oligonucleotides in biological environments (2). 2' F-ANA hybridizes strongly to target RNA and, unlike most 2' modifications, induces cleavage of the target by RNase H. Phosphorothioate (PS) 2' F-ANA is routinely used in these applications due to its increased nuclease resistance. Alternating 2' F-ANA and DNA units provide among the highest potency RNase H-activating oligomers. Both the "altimer" and "gapmer" strand architectures consistently outperform PS-DNA and DNA/RNA gapmers (4).

siRNA oligos were found to tolerate the presence of 2'-F-ANA linkages very well. High potency gene silencing was demonstrated5 with siRNA chimeras containing 2'-F-RNA and/or LNA and 2'-F-ANA. The high efficacy of these chimeras was attributed to the combination of the rigid RNA-like properties of 2'-F-RNA and LNA with the DNA-like properties of 2'-F-ANA.


Additional Recommended Reading

Glen Report 22.13.


References

  1. E. Viazovkina, M.M. Mangos, M.I. Elzagheid, and M.J. Damha, Curr Protoc Nucleic Acid Chem, 2002, Chapter 4, Unit 4 15.
  2. J.K. Watts, and M.J. Damha, Can. J. Chem., 2008, 86, 641-656.
  3. J.K. Watts, A. Katolik, J. Viladoms, and M.J. Damha, Org Biomol Chem, 2009, 7, 1904-10.
  4. A. Kalota, et al., Nucleic Acids Res., 2006, 34, 451.
  5. G.F. Deleavey, et al., Nucleic Acids Res., 2010, 38, 4547-4557, J.K. Watts, et al., Nucleic Acids Res., 2007, 35, 1441-1451, T. Dowler, et al., Nucleic Acids Res., 2006, 34, 1669-1675.
  6. Intellectual Property

    2'-F-ANA is covered by intellectual property. Key patents covering siRNA and antisense applications are as follows: WO/2009/146556 (siRNA); WO 03064441 and WO 0220773 (antisense).

    - 2'-fluoroarabinoside-Base (FANA-N)

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