Oligonucleotide Synthesis, RNA Raw Materials & Modification

5'-O-DMT-N6-phenoxyacetyl-2'-deoxyadenosine

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH64108CAS号110522-82-2纯度99.62%

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产品概述

快速信息

产品系列: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C39H37N5O7
分子量: 687.74
纯度: 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.

同义词

5'-O-DMT-N6-phenoxyacetyl-2'-deoxyadenosine; 5'-O-(4,4'-dimethoxytrityl)-N6-PAc-dA; DMT-dA(PAc)

身份与规格

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%

储存条件

2-8 C

技术属性

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

应用背景

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.

公开来源

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 化合物 13888002
PubChem · CID 13888002

常见问题

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.