2'-F-ANA-C (Bz) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C46H51FN5O8P
- MW
- 851.9
- Purity
- 99.84%
2'-F-ANA-C (Bz) CE Phosphoramidite is a 2'-deoxy-2'-fluoro-arabinonucleoside (2'F-ANA) building block: 5'-O-(4,4'-dimethoxytrityl)-N4-benzoyl-2'-deoxy-2'-fluoro-arabinocytidine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 1404463-12-2, molecular formula C46H51FN5O8P, molecular weight 851.9, PubChem CID 127263181, and InChIKey CKKJPMGSTGVCJJ-OEJVQKCDSA-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. Because C2' carries fluorine rather than a hydroxyl, no 2'-protecting group is needed; the monomer couples through a standard 3'-phosphoramidite (3'→5' linkages), the 5'-DMT is removed each cycle, and the N4-benzoyl base-protecting group is removed during final deprotection.
Synonyms
5'-O-DMT-N4-Bz-2'F-ANA-C 3'-CE phosphoramidite; 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl cytosine amidite
Identity and specifications
| Catalog No. | CH65071 |
| CAS No. | 1404463-12-2 |
| Molecular Formula | C46H51FN5O8P |
| Molecular Weight | 851.9 |
| PubChem CID | 127263181 |
| InChIKey | CKKJPMGSTGVCJJ-OEJVQKCDSA-N |
| Purity | 99.84% |
Storage conditions
-20 C
Technical attributes
- Monomer class
- 2'F-ANA CE phosphoramidite
- Nucleobase
- Cytosine
- Sugar configuration
- 2'-Deoxy-2'-fluoro-arabino
- Base protection
- N4-benzoyl
- Packaging
- 5 mg; 10 mg; 25 mg; 50 mg; 100 mg; 250 mg; 500 mg; 1 g; 5 g; 10 g; 25 g; supplied solution 1 mL; Custom packaging on request
- Solution concentration
- 10 mM in DMSO
- 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; the 5'-DMT is removed each cycle and the N4-benzoyl base-protecting group is removed during final deprotection. No 2'-protecting group is needed (C2' bears fluorine, not a hydroxyl).
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
- Chemical synthesis of RNA using fast oligonucleotide deprotection chemistry
Vinayak R, Anderson P, McCollum C, Hampel A
Nucleic Acids Research · 1992 · 20(6) · 1265-1269
- PubChem Compound 127263181
PubChem · CID 127263181
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.
Are 2'F-ANA/RNA duplexes cleaved by RNase H?
The cited 2'F-ANA literature reports RNase H substrate behavior for 2'F-ANA/RNA duplexes. This page uses that point only to explain the nucleic-acid chemistry context for the 2'F-ANA class.
What identifiers should match for CH65071?
Match CAS 1404463-12-2, molecular formula C46H51FN5O8P, molecular weight 851.9, PubChem CID 127263181, and InChIKey CKKJPMGSTGVCJJ-OEJVQKCDSA-N.
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