3'-O-TBDMS-Adenosine (Bz) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Produktübersicht
Kurzüberblick
- Produktfamilie
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C53H66N7O8PSi
- MW
- 988.2
- Reinheit
- 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.
Synonyme
5'-O-DMT-3'-O-TBDMS-N6-benzoyladenosine 2'-CE phosphoramidite; 2'-phosphoramidite regioisomer
Identität und Spezifikationen
| 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% |
Lagerbedingungen
-18 C
Technische Merkmale
- 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
Anwendungskontext
- 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.
Zugehörige technische Ressourcen
Öffentliche Quellen
- 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-Verbindung 14376009
PubChem · CID 14376009
Häufig gestellte Fragen
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).
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