Oligonucleotide Synthesis, RNA Raw Materials & Modification

3'-O-TBDMS-Uridine CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65066CAS号129451-77-0纯度>=98%

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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: C45H61N4O9PSi
分子量: 861.0
纯度: >=98%

3'-O-TBDMS-Uridine CE Phosphoramidite is a regioisomeric RNA building block: 5'-O-(4,4'-dimethoxytrityl)-uridine with a 3'-O-(tert-butyldimethylsilyl) group and a 2'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65066 is identified by CAS 129451-77-0, molecular formula C45H61N4O9PSi, molecular weight 861.0, PubChem CID 14376044, and InChIKey UZVSHRLVIXPYEZ-ZMHKPELYSA-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 and the 3'-O-TBDMS protects the 3'-hydroxyl. Because uracil has no exocyclic amine, no base protecting group is required.

同义词

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

身份与规格

Catalog No.	CH65066
CAS No.	129451-77-0
Molecular Formula	C45H61N4O9PSi
Molecular Weight	861.0
PubChem CID	14376044
InChIKey	UZVSHRLVIXPYEZ-ZMHKPELYSA-N
Purity	>=98%

储存条件

-20 +/- 5 C

技术属性

Monomer class: Regioisomeric RNA CE phosphoramidite
Nucleobase: Uracil
3'-O protection: TBDMS
Coupling position: 2'-O phosphoramidite
Packaging: 50 mg; 100 mg; 250 mg; 1 g; 5 g; 25 g; Custom packaging on request
Physical form: white to light yellow powder
Stability: in solvent 6 months at -80 C; in solvent 1 month at -20 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.
No base protection needed: uracil has no exocyclic amine, so this monomer requires no base protecting group.

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 14376044
PubChem · CID 14376044

常见问题

How does this differ from the standard 2'-O-TBDMS-rU 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.

Why does the 3'-O-TBDMS-rU amidite have no base protecting group?

Uracil has no reactive exocyclic amine, so it needs no base protection. The monomer carries a 5'-O-DMT group (removed each cycle), a 3'-O-TBDMS group (protects the 3'-hydroxyl), and the 2'-phosphoramidite coupling group.