2'-O,4'-C-Methyleneadenosine

Name: 2'-O,4'-C-Methyleneadenosine
Brand: ChemScene
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CAS No. 206055-70-1
Cat. No. CS-0042423
Purity≥96%
MDL No.MFCD18643183

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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General Information

CAS No. 206055-70-1
Cat. No. CS-0042423
Purity ≥96%
MDL No. MFCD18643183
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₃N₅O₄
Molecular Weight 279.25
Synonym(s) LNA-A
SMILES OC[C@]1(CO2)[C@@H](O)[C@@H]2[C@H](N3C(N=CN=C4N)=C4N=C3)O1

Description

2'-O,4'-C-Methyleneadenosine features a constrained ribose mimic with methylene bridges at the 2' and 4' positions, locking the sugar in a rigid C3'-endo conformation. This structural rigidity enhances nuclease resistance while preserving favorable base pairing geometry, making it ideal for antisense oligonucleotide synthesis and RNA-targeted therapeutics.

Application

2'-O,4'-C-Methyleneadenosine serves as a conformationally restricted nucleoside building block, enabling the synthesis of oligonucleotides with enhanced nuclease resistance and improved binding affinity. The methylene bridge locks the ribose in a C3'-endo sugar pucker, stabilizing the A-form helix geometry. This structural rigidity enhances duplex stability and is particularly valuable in antisense therapeutics and RNA-targeted drug development.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 128.54
LogP -1.5719
H_Acceptors 9
H_Donors 3
Rotatable_Bonds 2

Other Classifications

Life Science Nucleosides & Nucleotides Other Protective Nucleosides

Chemical Biology Nucleic Acid Chemistry Protected Nucleosides

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleobases and their Analogs

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleoside Analogs

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleosides

Key Words

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2'-O,4'-C-Methyleneadenosine

CAS No. 206055-70-1

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