Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-F-ANA-A (Bz) CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

製品番号CH65067CAS番号329187-86-2純度99.98%

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製品概要

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製品ファミリー: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C47H51FN7O7P
分子量: 875.9
純度: 99.98%

2'-F-ANA-A (Bz) CE Phosphoramidite is a 2'-deoxy-2'-fluoro-arabinonucleoside (2'F-ANA) building block: 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2'-deoxy-2'-fluoro-arabinoadenosine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. CH65067 is identified by CAS 329187-86-2, molecular formula C47H51FN7O7P, molecular weight 875.9, PubChem CID 124587489, and InChIKey VCCMVPDSLHFCBB-SAHKUVNLSA-N.

In 2'F-ANA the sugar is arabino-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 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 N6-benzoyl base group is removed at final deprotection.

別名

5'-O-DMT-N6-Bz-2'F-ANA-A 3'-CE phosphoramidite; 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl adenine amidite

同定情報と仕様

Catalog No.	CH65067
CAS No.	329187-86-2
Molecular Formula	C47H51FN7O7P
Molecular Weight	875.9
PubChem CID	124587489
InChIKey	VCCMVPDSLHFCBB-SAHKUVNLSA-N
Purity	99.98%

保管条件

powder -20 C; powder 4 C; in solvent -80 C; in solvent -20 C

技術属性

Monomer class: 2'F-ANA CE phosphoramidite
Nucleobase: Adenine
Sugar configuration: 2'-Deoxy-2'-fluoro-arabino
Base protection: N6-benzoyl
Packaging: 1 mg; 5 mg; 10 mg; 25 mg; 50 mg; 100 mg; 250 mg; 1 g; 5 g; 25 g; Custom packaging on request
Physical form: white to off-white solid powder
Stability: powder 3 years at -20 C; powder 2 years at 4 C; in solvent 6 months at -80 C; in solvent 1 month at -20 C

用途情報

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 N6-benzoyl base group is removed at final deprotection. No 2'-protecting group is needed (C2' bears fluorine, not a hydroxyl).

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
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 124587489
PubChem · CID 124587489

よくある質問

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.