3'-O-TBDMS-Guanosine (iBu) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C50H68N7O9PSi
- PM
- 970.2
- Pureté
- 99.1% (HPLC)
3'-O-TBDMS-Guanosine (iBu) CE Phosphoramidite is a regioisomeric RNA building block: 5'-O-(4,4'-dimethoxytrityl)-N2-isobutyrylguanosine with a 3'-O-(tert-butyldimethylsilyl) group and a 2'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65065 is identified by CAS 1445905-51-0, molecular formula C50H68N7O9PSi, molecular weight 970.2, PubChem CID 135742514, and InChIKey JCCWPNDXSMAHGZ-FTZVBZPOSA-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 N2-isobutyryl base group is removed at final deprotection.
Synonymes
5'-O-DMT-3'-O-TBDMS-N2-isobutyrylguanosine 2'-CE phosphoramidite; 2'-phosphoramidite regioisomer
Identité et spécifications
| Catalog No. | CH65065 |
| CAS No. | 1445905-51-0 |
| Molecular Formula | C50H68N7O9PSi |
| Molecular Weight | 970.2 |
| PubChem CID | 135742514 |
| InChIKey | JCCWPNDXSMAHGZ-FTZVBZPOSA-N |
| Purity | 99.1% (HPLC) |
Conditions de stockage
powder 2-8 C protected from light; in solvent -80 C; in solvent -20 C
Caractéristiques techniques
- Monomer class
- Regioisomeric RNA CE phosphoramidite
- Nucleobase
- Guanine
- 3'-O protection
- TBDMS
- Coupling position
- 2'-O phosphoramidite
- Packaging
- 25 mg; 50 mg; 100 mg; 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; Custom packaging on request
- Physical form
- solid
- 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.
- N2-isobutyryl base protection: the isobutyryl group masks the guanine exocyclic amine during synthesis and is removed at final deprotection.
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 135742514
PubChem · CID 135742514
Questions fréquentes
How does this differ from the standard 2'-O-TBDMS-rG(iBu) 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.
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