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
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- Nom chimique
- 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
- FM
- C43H52FN8O7P
- PM
- 842.9
- Pureté
- 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.
Synonymes
DMTr-2'-ara-F-dG(dmf)-3'-CE-phosphoramidite; 5'-O-DMT-N2-dmf-2'-deoxy-2'-fluoro-arabinoguanosine 3'-CE phosphoramidite
Identité et spécifications
| Catalog No. | CH65072 |
| CAS No. | 1391913-24-8 |
| Molecular Formula | C43H52FN8O7P |
| Molecular Weight | 842.9 |
| PubChem CID | 137166359 |
| InChIKey | BUKKJOTXODUNQK-ZZRCLNINSA-N |
| Purity | 98% |
Conditions de stockage
-20 C
Caractéristiques techniques
- 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
Contexte d’application
- 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.
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
- 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
- Composé PubChem 137166359
PubChem · CID 137166359
Questions fréquentes
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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