Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-Deoxyadenosine (Bz) CE Reverse Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65050CAS号140712-82-9纯度>=98.0% (HPLC)

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产品概述

快速信息

产品系列: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C47H52N7O7P
分子量: 857.9
纯度: >=98.0% (HPLC)

2'-Deoxyadenosine (Bz) CE Reverse Phosphoramidite is the reverse-orientation 2'-deoxyadenosine building block for DNA synthesis: N6-benzoyl-2'-deoxyadenosine with a 3'-O-(4,4'-dimethoxytrityl) group and a 5'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65050 is identified by CAS 140712-82-9, molecular formula C47H52N7O7P, molecular weight 857.9, PubChem CID 17998961, and InChIKey JMABKCCHUAJFJE-AKWFTNRHSA-N.

Unlike a standard amidite (DMT on 5', phosphoramidite on 3'), the reverse amidite has the DMT on the 3'-hydroxyl and the phosphoramidite on the 5'-hydroxyl, so chain elongation proceeds in the 5'→3' direction. The acid-labile 3'-DMT is removed each cycle, and the N6-benzoyl base group is removed at final deprotection.

同义词

reverse DMT-dA(Bz) phosphoramidite; 3'-O-DMT-N6-benzoyl-2'-deoxyadenosine 5'-CE phosphoramidite

身份与规格

Catalog No.	CH65050
CAS No.	140712-82-9
Molecular Formula	C47H52N7O7P
Molecular Weight	857.9
PubChem CID	17998961
InChIKey	JMABKCCHUAJFJE-AKWFTNRHSA-N
Purity	>=98.0% (HPLC)

储存条件

-20 C

技术属性

Monomer class: Reverse DNA CE phosphoramidite
Nucleobase: Adenine
DMT position: 3'-O
Coupling position: 5'-O phosphoramidite
Grade: N (Normal)
Packaging: 100 mg; 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; 100 g; Custom packaging on request
Water content: <=0.5%
Physical form: white to off-white powder
Stability: same in solution as standard dA phosphoramidite

应用背景

5'→3' DNA coupling monomer: the 5'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite is the reactive coupling group, so oligonucleotides grow in the 5'→3' direction (reverse of standard synthesis).
3'-DMT protection: the acid-labile 4,4'-dimethoxytrityl group is on the 3'-hydroxyl and is removed at the start of each chain-elongation cycle.
N6-benzoyl base protection: the benzoyl group masks the adenine exocyclic amine during synthesis and is removed at final deprotection.

公开来源

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 17998961
PubChem · CID 17998961

常见问题

What makes this a 'reverse' phosphoramidite?

In a standard amidite the DMT is on the 5'-hydroxyl and the phosphoramidite on the 3'-hydroxyl. Here they are swapped — 3'-DMT and 5'-phosphoramidite — so the oligonucleotide is assembled in the 5'→3' direction instead of the usual 3'→5'.

How does it relate to the standard 2'-deoxyadenosine (Bz) phosphoramidite?

It has the same N6-benzoyl-2'-deoxyadenosine core but the DMT and phosphoramidite are on the opposite hydroxyls (3' vs 5'). The standard (3'-phosphoramidite) dA(Bz) amidite is cataloged separately.