Oligonucleotide Synthesis, RNA Raw Materials & Modification

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

製品番号CH65072CAS番号1391913-24-8純度98%

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製品概要

クイックビュー

製品ファミリー: Oligonucleotide Synthesis, RNA Raw Materials & Modification
化学名: 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
分子式: C43H52FN8O7P
分子量: 842.9
純度: 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.

別名

DMTr-2'-ara-F-dG(dmf)-3'-CE-phosphoramidite; 5'-O-DMT-N2-dmf-2'-deoxy-2'-fluoro-arabinoguanosine 3'-CE phosphoramidite

同定情報と仕様

Catalog No.	CH65072
CAS No.	1391913-24-8
Molecular Formula	C43H52FN8O7P
Molecular Weight	842.9
PubChem CID	137166359
InChIKey	BUKKJOTXODUNQK-ZZRCLNINSA-N
Purity	98%

保管条件

-20 C

技術属性

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

用途情報

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.

公開情報源

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
PMID 11563058 DOI 10.1081/NCN-100002317
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
PMID 16421272 DOI 10.1093/nar/gkj455
The Degradation of dG Phosphoramidites in Solution
Hargreaves JS, Kaiser R, Wolber PK
Nucleosides, Nucleotides and Nucleic Acids · 2015 · 34(10) · 691-707
PMID 26397361 DOI 10.1080/15257770.2015.1071846
A new 2'-hydroxyl protecting group for the automated synthesis of oligoribonucleotides
Rastogi H, Usher DA
Nucleic Acids Research · 1995 · 23(23) · 4872-4877
PMID 8532531 DOI 10.1093/nar/23.23.4872
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
PMID 1373236 DOI 10.1093/nar/20.6.1265
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化合物 137166359
PubChem · CID 137166359

よくある質問

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.