5'-O-DMT-N6-phenoxyacetyl-2'-deoxyadenosine
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C39H37N5O7
- MW
- 687.74
- Purity
- 99.62%
5'-O-DMT-N6-phenoxyacetyl-2'-deoxyadenosine is 2'-deoxyadenosine carrying a 5'-O-(4,4'-dimethoxytrityl) (DMT) group and an N6-phenoxyacetyl (PAc) base-protecting group. CH64108 is identified by CAS 110522-82-2, molecular formula C39H37N5O7, molecular weight 687.74, PubChem CID 13888002, and InChIKey JDJUQANHKJNEFT-VUHKNJSWSA-N.
It is a doubly protected precursor for DNA phosphoramidite/oligonucleotide synthesis: the acid-labile 5'-DMT group is removed at the start of each chain-elongation cycle, while the labile N6-phenoxyacetyl group masks the adenine exocyclic amine and is removed at final deprotection.
Synonyms
5'-O-DMT-N6-phenoxyacetyl-2'-deoxyadenosine; 5'-O-(4,4'-dimethoxytrityl)-N6-PAc-dA; DMT-dA(PAc)
Identity and specifications
| Catalog No. | CH64108 |
| CAS No. | 110522-82-2 |
| Molecular Formula | C39H37N5O7 |
| Molecular Weight | 687.74 |
| PubChem CID | 13888002 |
| InChIKey | JDJUQANHKJNEFT-VUHKNJSWSA-N |
| Purity | 99.62% |
Storage conditions
2-8 C
Technical attributes
- Nucleobase
- Adenine
- Sugar
- 2'-Deoxyribose
- 5'-O protection
- DMT (dimethoxytrityl)
- Base protection
- N6-Phenoxyacetyl (PAc)
- Packaging
- 100 mg; 200 mg; 500 mg; 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: 2 years at 2-8 C; prepared stock solution: 6 months at -20 C or 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 oligonucleotide chain-elongation cycle.
- N6-phenoxyacetyl base protection: the labile PAc group masks the adenine exocyclic amine during synthesis and is removed at final deprotection.
- Phosphoramidite precursor context: a doubly protected 2'-deoxyadenosine precursor toward DNA phosphoramidite building blocks.
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 13888002
PubChem · CID 13888002
Frequently Asked Questions
What do the two protecting groups on this deoxyadenosine do?
The 5'-O-DMT (dimethoxytrityl) group is an acid-labile protection on the 5'-hydroxyl that is removed at the start of each oligonucleotide chain-elongation cycle; the N6-phenoxyacetyl (PAc) group is a labile protection on the adenine exocyclic amine, removed at final deprotection.
How does it differ from 5'-O-DMT-N6-benzoyl-2'-deoxyadenosine?
Both are 5'-O-DMT-protected 2'-deoxyadenosines with a protected adenine N6-amine, but this one uses a labile phenoxyacetyl (PAc) group rather than benzoyl. The benzoyl form is cataloged separately.
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