2'-F-ANA-G (dmf) CE Phosphoramidite
N'-[9-[(2R,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- Chemical Name
- N'-[9-[(2R,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
- MF
- C43H52FN8O7P
- MW
- 842.9
- Purity
- 98%
2'-F-ANA-G (dmf) CE Phosphoramidite is a protected 2'-deoxy-2'-fluoro-arabinoguanosine building block for modified-oligonucleotide synthesis. CH65072 carries a 5'-O-DMT group, N2-dimethylformamidine (dmf) guanine protection, and a 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. It is identified by CAS 1391913-24-8, molecular formula C43H52FN8O7P, molecular weight 842.9, PubChem CID 137166359, and InChIKey BUKKJOTXODUNQK-ZZRCLNINSA-N.
The fluorine at C2' has the arabino configuration, which distinguishes 2'F-ANA from ribo 2'-F-RNA. In solid-phase synthesis the 3'-phosphoramidite is the coupling group, the acid-labile 5'-DMT is removed during chain elongation, and the N2-dmf group is removed during final deprotection. Published 2'F-ANA studies provide context for arabino configuration and 2'F-ANA/RNA duplex behavior with RNase H.
Synonyms
DMTr-2'-ara-F-dG(dmf)-3'-CE-phosphoramidite; 5'-O-DMT-N2-dmf-2'-deoxy-2'-fluoro-arabinoguanosine 3'-CE phosphoramidite
Identity and specifications
| Catalog No. | CH65072 |
| CAS No. | 1391913-24-8 |
| Molecular Formula | C43H52FN8O7P |
| Molecular Weight | 842.9 |
| PubChem CID | 137166359 |
| InChIKey | BUKKJOTXODUNQK-ZZRCLNINSA-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-Dimethylformamidine (dmf)
- Packaging
- 10 mg; 50 mg; 100 mg; 250 mg; Custom packaging on request
- Physical form
- powder
- Stability
- powder: 3 years at -20 C
Application context
- 2'F-ANA oligonucleotide synthesis: an arabino-configured guanosine CE phosphoramidite for incorporation into modified oligonucleotides.
- Arabino 2'-fluoro chemistry: the C2' configuration distinguishes 2'F-ANA from ribo 2'-F-RNA; cited literature discusses 2'F-ANA/RNA duplex behavior with RNase H.
- Protected guanosine monomer: the 3'-phosphoramidite supports coupling, while 5'-DMT and N2-dmf provide temporary protection during chain assembly and final deprotection.
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 137166359
PubChem · CID 137166359
Frequently Asked Questions
How does 2'F-ANA differ from 2'-F-RNA?
Both contain fluorine at C2', but their configuration differs. CH65072 has the arabino configuration that defines 2'F-ANA, whereas 2'-F-RNA uses the ribo configuration.
What is the role of the protecting groups in CH65072?
The 5'-DMT group is removed during chain elongation, and the N2-dimethylformamidine group protects guanine until final deprotection. The 3'-CE phosphoramidite is the coupling group.
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