Oligonucleotide Synthesis, RNA Raw Materials & Modification

3'-O-TBDMS-Adenosine (Bz) CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65063CAS号129451-75-8纯度98.38%

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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: C53H66N7O8PSi
分子量: 988.2
纯度: 98.38%

3'-O-TBDMS-Adenosine (Bz) CE Phosphoramidite is a regioisomeric RNA building block: 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyladenosine with a 3'-O-(tert-butyldimethylsilyl) group and a 2'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65063 is identified by CAS 129451-75-8, molecular formula C53H66N7O8PSi, molecular weight 988.2, PubChem CID 14376009, and InChIKey HRYAQLIYKSXPET-RFMFGJHUSA-N.

Unlike the standard RNA amidite (2'-O-TBDMS, 3'-phosphoramidite), here the silyl group is on the 3'-hydroxyl and the phosphoramidite is on the 2'-hydroxyl. Coupling therefore forms 2'→5' internucleotide linkages. The acid-labile 5'-DMT is removed each cycle, the 3'-O-TBDMS protects the 3'-hydroxyl, and the N6-benzoyl base group is removed at final deprotection.

同义词

5'-O-DMT-3'-O-TBDMS-N6-benzoyladenosine 2'-CE phosphoramidite; 2'-phosphoramidite regioisomer

身份与规格

Catalog No.	CH65063
CAS No.	129451-75-8
Molecular Formula	C53H66N7O8PSi
Molecular Weight	988.2
PubChem CID	14376009
InChIKey	HRYAQLIYKSXPET-RFMFGJHUSA-N
Purity	98.38%

储存条件

-18 C

技术属性

Monomer class: Regioisomeric RNA CE phosphoramidite
Nucleobase: Adenine
3'-O protection: TBDMS
Coupling position: 2'-O phosphoramidite
Packaging: 100 mg; 250 mg; 500 mg; 1 g; 5 g; 10 g; 25 g; 50 g; 100 g; 150 g; 500 g; 1 kg; 5 kg; 10 kg; 1 mL (10 mM in DMSO); Custom packaging on request
Solution concentration: 10 mM in DMSO
Physical form: solid white to off-white
Stability: powder 2 years; in solvent 6 months at -20 C; in solvent 1 year at -80 C

应用背景

2'→5' linkage coupling monomer: the 2'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite is the reactive coupling group, so internucleotide bonds form between the 2'-position and the next 5'-hydroxyl (2'→5' linkages).
5'-DMT + 3'-O-TBDMS protection: the acid-labile 5'-DMT is removed each cycle, while the 3'-O-TBDMS group protects the 3'-hydroxyl during synthesis.
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 14376009
PubChem · CID 14376009

常见问题

How does this differ from the standard 2'-O-TBDMS-rA(Bz) amidite?

It is the regioisomer: the TBDMS group is on the 3'-hydroxyl and the phosphoramidite is on the 2'-hydroxyl (swapped versus the standard amidite). Coupling through the 2'-phosphoramidite forms 2'→5' internucleotide linkages instead of the usual 3'→5' linkages.

What linkage does this amidite form?

Because the phosphoramidite is on the 2'-position, coupling forms 2'→5' internucleotide linkages (as found, for example, in 2'-5'-linked oligoadenylates).