3'-O-TBDMS-Uridine CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C45H61N4O9PSi
- PM
- 861.0
- Pureté
- >=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.
Synonymes
5'-O-DMT-3'-O-TBDMS-uridine 2'-CE phosphoramidite; 2'-phosphoramidite regioisomer
Identité et spécifications
| Catalog No. | CH65066 |
| CAS No. | 129451-77-0 |
| Molecular Formula | C45H61N4O9PSi |
| Molecular Weight | 861.0 |
| PubChem CID | 14376044 |
| InChIKey | UZVSHRLVIXPYEZ-ZMHKPELYSA-N |
| Purity | >=98% |
Conditions de stockage
-20 +/- 5 C
Caractéristiques techniques
- 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
Contexte d’application
- 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.
Ressources techniques associées
Sources publiques
- 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
- Composé PubChem 14376044
PubChem · CID 14376044
Questions fréquentes
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.
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