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Sigma-Aldrich

Cholesteryl-TEG azide

Synonym(s):

3-(13-azido-5,8,11-trioxa-2-azatridecanoate) cholesterol

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About This Item

Empirical Formula (Hill Notation):
C36H62N4O5
CAS Number:
1391826-58-6
Molecular Weight:
630.90
UNSPSC Code:
12352125
PubChem Substance ID:
329768444
NACRES:
NA.22

form

solid

Quality Level

100

storage temp.

−20°C

SMILES string

CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](OC(NCCOCCOCCOCCN=[N+]=[N-])=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C

InChI

1S/C36H62N4O5/c1-26(2)7-6-8-27(3)31-11-12-32-30-10-9-28-25-29(13-15-35(28,4)33(30)14-16-36(31,32)5)45-34(41)38-17-19-42-21-23-44-24-22-43-20-18-39-40-37/h9,26-27,29-33H,6-8,10-25H2,1-5H3,(H,38,41)/t27-,29+,30+,31-,32+,33+,35+,36-/m1/s1

InChI key

POWZASPNLQFLJO-MKQVXYPISA-N

Application

Cholesteryl-TEG azide is an azide-containing cholesterol derivative that can be used as a reagent in the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction to install a cholesteryl tag. It is also reported in the construction of novel anandamide-siRNA conjugates.

Other Notes

Click-Modified Anandamide siRNA Enables Delivery and Gene Silencing in Neuronal and Immune Cells

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Julian Willibald et al.
Journal of the American Chemical Society, 134(30), 12330-12333 (2012-07-21)
Click chemistry of alkyne-modified RNA with different receptor ligand azides was used to prepare 3'-folate, 3'-cholesterol, and, as a new entity, 3'-anandamide-modified RNA in high yields and excellent purity. The anandamide-modified RNA shows surprisingly high transfection properties and enables the
Natalia Kleczewska et al.
Chemical science, 12(30), 10242-10251 (2021-08-12)
Targeting cap-dependent translation initiation is one of the experimental approaches that could lead to the development of novel anti-cancer therapies. Synthetic dinucleoside 5',5'-triphosphates cap analogs are potent antagonists of eukaryotic translation initiation factor 4E (eIF4E) in vitro and could counteract

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