CHEMOS
Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-O-Propargyl-C (Ac) CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

Produkt-Nr.CH65074CAS-Nr.1498305-51-3Reinheit98%
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Produktübersicht

Kurzüberblick

Produktfamilie
Oligonucleotide Synthesis, RNA Raw Materials & Modification
MF
C44H52N5O9P
MW
825.9
Reinheit
98%

2'-O-Propargyl-C (Ac) CE Phosphoramidite is a click-handle RNA building block: 5'-O-(4,4'-dimethoxytrityl)-N4-acetyl-2'-O-(prop-2-yn-1-yl)cytidine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 1498305-51-3, molecular formula C44H52N5O9P, molecular weight 825.9, PubChem CID 170899159, and InChIKey JIMYWWYYWAHJAD-ZMHKPELYSA-N.

The 2'-O-propargyl group is a permanent 2'-O-ether that carries a terminal alkyne (C≡CH) — it is not a protecting group. That terminal alkyne is a "click" handle: oligonucleotides bearing a terminal alkyne can be labeled after synthesis by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) with azide-bearing reporters. The monomer couples through a standard 3'-phosphoramidite (3'→5' linkages), the 5'-DMT is removed each cycle, and the N4-acetyl base group is removed at final deprotection.

Synonyme

5'-O-DMT-N4-Ac-2'-O-propargylcytidine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-cytidine amidite

Identität und Spezifikationen

Catalog No.CH65074
CAS No.1498305-51-3
Molecular FormulaC44H52N5O9P
Molecular Weight825.9
PubChem CID170899159
InChIKeyJIMYWWYYWAHJAD-ZMHKPELYSA-N
Purity98%

Lagerbedingungen

-20 C

Technische Merkmale

Monomer class
2'-O-propargyl CE phosphoramidite
Nucleobase
Cytosine
Conjugation handle
Terminal alkyne
Base protection
N4-acetyl
Packaging
100 mg; 250 mg; 500 mg; 1 g; 5 g; 10 g; 100 g; 1 kg; Custom packaging on request
Physical form
white, off-white to faint yellow powder

Anwendungskontext

  • Internal click handle: the 2'-O-propargyl ether places a terminal alkyne at the 2'-position for post-synthetic conjugation.
  • CuAAC labeling: the terminal alkyne reacts with azide-bearing reporters (dyes, biotin, other tags) by the copper-catalyzed azide-alkyne cycloaddition (click chemistry).
  • 3'→5' coupling monomer: the 3'-phosphoramidite couples to form 3'→5' linkages; the 5'-DMT is removed each cycle and the N4-acetyl base-protecting group is removed during final deprotection.

Zugehörige technische Ressourcen

Oligonukleotid-Modifikation

Zucker-, Basen-, Backbone-, terminale und Konjugationsmodifikationen für ASO, siRNA, guide RNA, Aptamere und Oligos.

Oligonukleotid-Synthese

Support für modifizierte Monomere, Supports, Sulfurisierungsreagenzien, Cap-Analoga und verwandte Oligo-Syntheseinputs.

Öffentliche Quellen

Häufig gestellte Fragen

What does the 2'-O-propargyl group provide?

It is a permanent 2'-O-ether that carries a terminal alkyne. The alkyne is a 'click' handle: after synthesis, the oligonucleotide can be conjugated to azide-bearing reporters (dyes, biotin, etc.) by the copper-catalyzed azide-alkyne cycloaddition (CuAAC).

Why is the cytosine acetyl-protected?

The N4-acetyl group masks the cytosine exocyclic amine during synthesis and is removed at final deprotection. The 5'-DMT is removed each coupling cycle, while the 2'-O-propargyl ether stays on the finished oligonucleotide as the click handle.

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