2’-F-Arabinonucleic Acid (2’-F-ANA) (Catalog as PDF)

2’-F-Arabinonucleic Acid (2’-F-ANA)

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 β-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 (DTm1.2°C/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 -7.2°C and in a 2'-F-ANA - DNA duplex a DTm of -3.9°C.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.
Item Catalog No. Pack Price ($)
10-3800-90 100µm 150.00
10-3800-02 0.25g 375.00
10-3810-02 0.25g Discontinued
10-3810-05 0.5g Discontinued
  2'-F-C-ANA-CE Phosphoramidite has been discontinued. The substitute is : 2'-F-Ac-C-ANA-CE Phosphoramidite
10-3815-02 0.25g 200.00
10-3815-05 0.5g 400.00
10-3820-90 100µm 165.00
10-3820-02 0.25g 425.00
10-3830-02 0.25g 125.00
10-3830-05 0.5g 250.00
2'-F-A-ANA
2'-F-A-ANA
2'-F-Ac-C-ANA
2'-F-Ac-C-ANA
2'-F-G-ANA
2'-F-G-ANA
2'-F-U-ANA
2'-F-U-ANA

STABILITY NOTE

Synthetic oligonucleotides containing 2'-F-RNA linkages may be deprotected with ammonium hydroxide as normal. Deprotection using AMA at 65°C leads to some degradation and so we recommend the use of AMA at room temperature for 2 hours.

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).

Reference(s)

  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.

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