Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-O-TBDMS-Uridine CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65013CAS号118362-03-1纯度100% (NMR)

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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: 100% (NMR)

2'-O-TBDMS-Uridine CE Phosphoramidite is the uridine building block for RNA synthesis: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-uridine bearing a 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65013 is identified by CAS 118362-03-1, molecular formula C45H61N4O9PSi, molecular weight 861.0, PubChem CID 10898199, and InChIKey SKNLXHRBXYGJOC-ZMHKPELYSA-N.

Nucleoside phosphoramidites are the coupling monomers used in automated solid-phase RNA synthesis: the 3'-phosphoramidite is the reactive group that couples to the growing chain, the acid-labile 5'-DMT is removed at the start of each cycle, and the 2'-O-TBDMS protects the ribose 2'-hydroxyl. Because uracil has no exocyclic amine, no base protecting group is required.

同义词

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

身份与规格

Catalog No.	CH65013
CAS No.	118362-03-1
Molecular Formula	C45H61N4O9PSi
Molecular Weight	861.0
PubChem CID	10898199
InChIKey	SKNLXHRBXYGJOC-ZMHKPELYSA-N
Purity	100% (NMR)

储存条件

-20 C; dry, inert atmosphere

技术属性

Monomer class: RNA CE phosphoramidite
Nucleobase: Uracil
2'-O protection: TBDMS (tert-butyldimethylsilyl)
Base protection: Unprotected
Grade: N (Normal)
Packaging: 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; 25 g; 50 g; 100 g; 200 g; Custom packaging on request
Water content: K.F. <=0.20% w/w
Physical form: white to light yellow powder
Stability: Manufactured 2023-10-24; retest 2027-04-26; expiry 2027-10-23

应用背景

RNA coupling monomer: the 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite is the reactive group that couples to the growing oligonucleotide chain in automated solid-phase RNA synthesis.
5'-DMT + 2'-O-TBDMS protection: the acid-labile 5'-DMT is removed each cycle, while the 2'-O-TBDMS group protects the ribose 2'-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 10898199
PubChem · CID 10898199

常见问题

Why does the uridine RNA phosphoramidite have no base protecting group?

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

How does it relate to 5'-O-DMT-2'-O-TBDMS-uridine?

It is the phosphoramidite of that nucleoside: the 3'-hydroxyl has been converted to a 2-cyanoethyl N,N-diisopropyl phosphoramidite. The precursor is cataloged separately.