2'-F-ANA-U CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C39H46FN4O8P
- PM
- 748.8
- Pureté
- >=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.
Synonymes
5'-O-DMT-2'F-ANA-U 3'-CE phosphoramidite; 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl uracil amidite
Identité et spécifications
| Catalog No. | CH65070 |
| CAS No. | 1190089-70-3 |
| Molecular Formula | C39H46FN4O8P |
| Molecular Weight | 748.8 |
| PubChem CID | 99651534 |
| InChIKey | HQHQPAYRJJMYQX-CPBIVIIKSA-N |
| Purity | >=98% |
Conditions de stockage
-20 C
Caractéristiques techniques
- 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
Contexte d’application
- 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.
Ressources techniques associées
Sources publiques
- 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
- Composé PubChem 99651534
PubChem · CID 99651534
Questions fréquentes
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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