Oligonucleotide Synthesis, RNA Raw Materials & Modification

5'-O-DMT-2'-O-TBDMS-N4-acetylcytidine

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH64111CAS号121058-85-3纯度99.80% (LC-MS)

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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: C38H47N3O8Si
分子量: 701.9
纯度: 99.80% (LC-MS)

5'-O-DMT-2'-O-TBDMS-N4-acetylcytidine is cytidine carrying three protecting groups: a 5'-O-(4,4'-dimethoxytrityl) (DMT) group, a 2'-O-(tert-butyldimethylsilyl) (TBDMS) group, and an N4-acetyl base-protecting group. CH64111 is identified by CAS 121058-85-3, molecular formula C38H47N3O8Si, molecular weight 701.9, PubChem CID 11136250, and InChIKey ZFRWPAYPCFTQHK-HYGOWAQNSA-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 N4-acetyl group masks the cytosine exocyclic amine and is removed at final deprotection.

同义词

5'-O-DMT-2'-O-TBDMS-N4-acetylcytidine; 5'-O-DMT-2'-O-tert-butyldimethylsilyl-N4-Ac-rC; DMT-2'-TBDMS-rC(Ac)

身份与规格

Catalog No.	CH64111
CAS No.	121058-85-3
Molecular Formula	C38H47N3O8Si
Molecular Weight	701.9
PubChem CID	11136250
InChIKey	ZFRWPAYPCFTQHK-HYGOWAQNSA-N
Purity	99.80% (LC-MS)

储存条件

2-8 C

技术属性

Nucleobase: Cytosine
5'-O protection: DMT (dimethoxytrityl)
2'-O protection: TBDMS (tert-butyldimethylsilyl)
Base protection: N4-Acetyl
Packaging: 100 mg; 500 mg; 1 g; 5 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: User-prepared stock solution: 6 months at -80 C or 1 month at -20 C; protect from light

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 RNA chain-elongation cycle.
2'-O-TBDMS 2'-OH protection: the tert-butyldimethylsilyl group protects the ribose 2'-hydroxyl during solid-phase RNA synthesis.
N4-acetyl base protection: the acetyl group masks the cytosine exocyclic amine during synthesis and is removed at final deprotection.

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 11136250
PubChem · CID 11136250

常见问题

What do the three protecting groups on this cytidine 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 N4-acetyl group protects the cytosine exocyclic amine, removed at final deprotection.

How does it differ from 5'-O-DMT-2'-O-TBDMS-N4-benzoylcytidine?

Both are 5'-O-DMT-2'-O-TBDMS-protected cytidines with a protected cytosine N4-amine, but this one uses an acetyl group rather than benzoyl. The benzoyl form is cataloged separately.