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Merck

762024

Azide-PEG3-biotin conjugate

Synonym(s):

Polyethylene glycol, N-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethyl]hexahydro-2-oxo-(3aS,4S,6aR)- 1H-thieno[3,4-d ]imidazole-4-pentanamide, Biotin-PEG3-azide

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About This Item

Empirical Formula (Hill Notation):
C18H32N6O5S
CAS Number:
Molecular Weight:
444.55
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352125
MDL number:
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form

solid

Quality Level

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

SMILES string

O=C1N[C@](CS[C@H]2CCCCC(NCCOCCOCCOCCN=[N+]=[N-])=O)([H])[C@]2([H])N1

InChI

1S/C18H32N6O5S/c19-24-21-6-8-28-10-12-29-11-9-27-7-5-20-16(25)4-2-1-3-15-17-14(13-30-15)22-18(26)23-17/h14-15,17H,1-13H2,(H,20,25)(H2,22,23,26)/t14-,15-,17-/m1/s1

InChI key

ZWFOOMQCYIGZBE-BFYDXBDKSA-N

Application

Azide-PEG3-biotin conjugate has been used for the detection of a cellular alkyne cholesterol analog via click chemistry using fluorescence microscopy after incubation with a fluorescent streptavidin-conjugate. It has also been used to prepare a novel multifunctional benzophenone linker that can be used for pull-down assays, photoaffinity labeling and double-click stapling techniques.
Biotinylation reagent for labeling alkyne containing molecules or biomolecules using either copper-catalyzed 1,3 dipolar cycloaddition click chemistry or copper-free click chemistry with cyclooctyne derivatives. The azide group reacts with alkynes to form a stable triazole linkage facilitating the introduction of biotin into your alkyne modified system of interest. This reaction is bioorthogonal or in other words compatible with biological systems in that it′s components do not react with the biological environment.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Chapter Five-Mapping Lysine Acetyltransferase?Ligand Interactions by Activity-Based Capture
Montgomery DC & Meier JL
Methods in Enzymology, 574, 105-123 (2016)
A novel alkyne cholesterol to trace cellular cholesterol metabolism and localization.
Hofmann K, et al.
Journal of Lipid Research, 55(3), 583-591 (2014)
Development of a Multifunctional Benzophenone Linker for Peptide Stapling and Photoaffinity Labelling
Wu Y, et al.
Chembiochem, 17(8), 689-692 (2016)