2'-F-ANA-U CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C39H46FN4O8P
- MW
- 748.8
- Purity
- >=98%
2'-F-ANA-U CE Phosphoramidite is a 2'-deoxy-2'-fluoro-arabinonucleoside (2'F-ANA) building block: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-fluoro-arabinouridine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 1190089-70-3, molecular formula C39H46FN4O8P, molecular weight 748.8, PubChem CID 99651534, and InChIKey HQHQPAYRJJMYQX-CPBIVIIKSA-N.
In 2'F-ANA the sugar is an arabinose configured at C2' — the fluorine sits on the face opposite that of a 2'-ribo substituent, which distinguishes 2'F-ANA from 2'-F-RNA. The cited 2'F-ANA literature discusses arabino C2' configuration and 2'F-ANA/RNA duplex behavior with RNase H. Uracil has no exocyclic amine, so no base protecting group is needed; C2' carries fluorine rather than a hydroxyl, so no 2'-protecting group is needed either. The monomer couples through a standard 3'-phosphoramidite (3'→5' linkages) and the 5'-DMT is removed each cycle.
Synonyms
5'-O-DMT-2'F-ANA-U 3'-CE phosphoramidite; 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl uracil amidite
Identity and specifications
| Catalog No. | CH65070 |
| CAS No. | 1190089-70-3 |
| Molecular Formula | C39H46FN4O8P |
| Molecular Weight | 748.8 |
| PubChem CID | 99651534 |
| InChIKey | HQHQPAYRJJMYQX-CPBIVIIKSA-N |
| Purity | >=98% |
Storage conditions
-20 C
Technical attributes
- Monomer class
- 2'F-ANA CE phosphoramidite
- Nucleobase
- Uracil
- Sugar configuration
- 2'-Deoxy-2'-fluoro-arabino
- Base protection
- None required
- Packaging
- 10 mg; 25 mg; 50 mg; 100 mg; 250 mg; 500 mg; 1 g; 5 g; 25 g; Custom packaging on request
- Water content
- <=0.5%
- Physical form
- white to off-white powder
- Stability
- powder 3 years; in solvent 1 year
Application context
- Arabino 2'-fluoro sugar: the fluorine at C2' is in the arabino configuration (distinct from ribo 2'-F-RNA), the defining structural feature of 2'F-ANA.
- RNase H literature context: the cited 2'F-ANA literature discusses 2'F-ANA/RNA duplex behavior with RNase H.
- 3'→5' coupling monomer: the 3'-phosphoramidite couples to form 3'→5' linkages and the 5'-DMT is removed each cycle. Uracil needs no base protection, and C2' bears fluorine (not a hydroxyl), so no 2'-protecting group is needed.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- Properties of arabinonucleic acids (ANA & 2'F-ANA): implications for the design of antisense therapeutics that invoke RNase H cleavage of RNA
Damha MJ, Noronha AM, Wilds CJ, Trempe JF, Denisov A, Pon RT, Gehring K
Nucleosides, Nucleotides and Nucleic Acids · 2001 · 20(4-7) · 429-440
- 2'-Deoxy-2'-fluoro-beta-D-arabinonucleic acid (2'F-ANA) modified oligonucleotides (ON) effect highly efficient, and persistent, gene silencing
Kalota A, Karabon L, Swider CR, Viazovkina E, Elzagheid M, Damha MJ, Gewirtz AM
Nucleic Acids Research · 2006 · 34(2) · 451-461
- A new 2'-hydroxyl protecting group for the automated synthesis of oligoribonucleotides
Rastogi H, Usher DA
Nucleic Acids Research · 1995 · 23(23) · 4872-4877
- Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing
Journal of Organic Chemistry, 2021
Product-family technical context
- Solid-phase supports for oligonucleotide synthesis
Current Protocols in Nucleic Acid Chemistry, 2013
Product-family technical context
- Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis
Tetrahedron Letters, 1981
Product-family technical context
- Synthesis of deoxyoligonucleotides on a polymer support
Journal of the American Chemical Society, 1981
Product-family technical context
- PubChem Compound 99651534
PubChem · CID 99651534
Frequently Asked Questions
How does 2'F-ANA differ from 2'-F-RNA?
Both carry a fluorine at C2', but the configuration differs: 2'F-ANA is arabino (fluorine on the opposite face), whereas 2'-F-RNA is ribo. This arabino configuration is the defining structural feature of 2'F-ANA.
Does the 2'F-ANA-U amidite need a base protecting group?
No. Uracil has no reactive exocyclic amine, so it needs no base protection. The monomer carries a 5'-O-DMT group (removed each cycle) and a 3'-phosphoramidite coupling group; C2' bears fluorine, so no 2'-protecting group is used.
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