2'-F-ANA-G (iBu) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C44H53FN7O8P
- MW
- 857.9
- Purity
- >=98%
2'-F-ANA-G (iBu) CE Phosphoramidite is a 2'-deoxy-2'-fluoro-arabinonucleoside (2'F-ANA) building block: 5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-2'-deoxy-2'-fluoro-arabinoguanosine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 1404463-20-2, molecular formula C44H53FN7O8P, molecular weight 857.9, PubChem CID 137213540, and InChIKey KJFUMXZZVYMQEU-SJIRJWTBSA-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 N2-isobutyryl base-protecting group is removed during final deprotection.
Synonyms
5'-O-DMT-N2-iBu-2'F-ANA-G 3'-CE phosphoramidite; 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl guanine amidite
Identity and specifications
| Catalog No. | CH65069 |
| CAS No. | 1404463-20-2 |
| Molecular Formula | C44H53FN7O8P |
| Molecular Weight | 857.9 |
| PubChem CID | 137213540 |
| InChIKey | KJFUMXZZVYMQEU-SJIRJWTBSA-N |
| Purity | >=98% |
Storage conditions
-20 C
Technical attributes
- Monomer class
- 2'F-ANA CE phosphoramidite
- Nucleobase
- Guanine
- Sugar configuration
- 2'-Deoxy-2'-fluoro-arabino
- Base protection
- N2-isobutyryl
- Packaging
- 5 mg; 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
- >=4 years
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 N2-isobutyryl base-protecting group is removed during final deprotection. No 2'-protecting group is needed (C2' bears fluorine, not a hydroxyl).
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
- The Degradation of dG Phosphoramidites in Solution
Hargreaves JS, Kaiser R, Wolber PK
Nucleosides, Nucleotides and Nucleic Acids · 2015 · 34(10) · 691-707
- 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
- 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 137213540
PubChem · CID 137213540
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.
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