5'-O-DMT-2'-O-TBDMS-N2-isobutyrylguanosine
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C41H51N5O8Si
- MW
- 770.0
- Purity
- >=98.0%
5'-O-DMT-2'-O-TBDMS-N2-isobutyrylguanosine is guanosine carrying three protecting groups: a 5'-O-(4,4'-dimethoxytrityl) (DMT) group, a 2'-O-(tert-butyldimethylsilyl) (TBDMS) group, and an N2-isobutyryl base-protecting group. CH64112 is identified by CAS 81279-39-2, molecular formula C41H51N5O8Si, molecular weight 770.0, PubChem CID 135451092, and InChIKey JMCNKJFOIJGYRG-CJEGOSRCSA-N.
It is an RNA phosphoramidite precursor: the acid-labile 5'-DMT group is removed at the start of each chain-elongation cycle, the 2'-O-TBDMS group protects the ribose 2'-hydroxyl during RNA synthesis, and the N2-isobutyryl group masks the guanine exocyclic amine and is removed at final deprotection.
Synonyms
5'-O-DMT-2'-O-TBDMS-N2-isobutyrylguanosine; 5'-O-DMT-2'-O-tert-butyldimethylsilyl-N2-ibu-rG; DMT-2'-TBDMS-rG(iBu)
Identity and specifications
| Catalog No. | CH64112 |
| CAS No. | 81279-39-2 |
| Molecular Formula | C41H51N5O8Si |
| Molecular Weight | 770.0 |
| PubChem CID | 135451092 |
| InChIKey | JMCNKJFOIJGYRG-CJEGOSRCSA-N |
| Purity | >=98.0% |
Storage conditions
2-8 C
Technical attributes
- Nucleobase
- Guanine
- 5'-O protection
- DMT (dimethoxytrityl)
- 2'-O protection
- TBDMS (tert-butyldimethylsilyl)
- Base protection
- N2-Isobutyryl
- Packaging
- 100 mg; 200 mg; 500 mg; 1 g; 5 g; 10 g; 1 mL; Custom packaging on request
- Solution concentration
- 10 mM in DMSO
- Water content
- <=1.0%
- Physical form
- white to off-white powder
- Stability
- Powder: 3 years at -20 C; in solvent: 1 year at -80 C
Application context
- 5'-DMT 5'-OH protection: the acid-labile 4,4'-dimethoxytrityl group protects the 5'-hydroxyl and is removed at the start of each RNA chain-elongation cycle.
- 2'-O-TBDMS 2'-OH protection: the tert-butyldimethylsilyl group protects the ribose 2'-hydroxyl during solid-phase RNA synthesis.
- N2-isobutyryl base protection: the isobutyryl group masks the guanine exocyclic amine during synthesis and is removed at final deprotection.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- 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 Compound 135451092
PubChem · CID 135451092
Frequently Asked Questions
What do the three protecting groups on this guanosine do?
The 5'-O-DMT group is an acid-labile 5'-hydroxyl protection removed at the start of each RNA chain-elongation cycle; the 2'-O-TBDMS group protects the ribose 2'-hydroxyl during solid-phase RNA synthesis; and the N2-isobutyryl group protects the guanine exocyclic amine, removed at final deprotection.
How does it differ from 5'-O-DMT-N2-isobutyryl-2'-deoxyguanosine?
This is the ribonucleoside form with a 2'-hydroxyl protected as a 2'-O-TBDMS ether (for RNA synthesis), whereas the deoxy version has no 2'-OH. The 2'-deoxy form is cataloged separately.
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