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Merck
CN

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:
875770-34-6
Molecular Weight:
444.55
NACRES:
NA.22
PubChem Substance ID:
329766598
UNSPSC Code:
12352125
MDL number:
MFCD20134145

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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

SMILES string

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

InChI key

ZWFOOMQCYIGZBE-BFYDXBDKSA-N

form

solid

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

Quality Level

200

Related Categories

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4358
MKCX8189
MKCZ0491
MKCX7975
MKCX3805

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Development of a Multifunctional Benzophenone Linker for Peptide Stapling and Photoaffinity Labelling
Wu Y, et al.
Chembiochem, 17(8), 689-692 (2016)
Chapter Five-Mapping Lysine Acetyltransferase?Ligand Interactions by Activity-Based Capture
Montgomery DC & Meier JL
Methods in Enzymology, 574, 105-123 (2016)
Isotope-targeted glycoproteomics (IsoTaG) analysis of sialylated N-and O-glycopeptides on an Orbitrap Fusion Tribrid using azido and alkynyl sugars.
Woo CM, et al.
Analytical and Bioanalytical Chemistry, 409(2), 579-588 (2017)
A novel alkyne cholesterol to trace cellular cholesterol metabolism and localization.
Hofmann K, et al.
Journal of Lipid Research, 55(3), 583-591 (2014)
Qingfei Zheng et al.
The Journal of organic chemistry, 85(3), 1691-1697 (2019-12-26)
Methylglyoxal (MGO) is a reactive dicarbonyl metabolite that modifies histones in vivo and induces changes in chromatin structure and function. Here we report the synthesis and application of a chemical probe for investigating MGO-glycation. A two-step synthesis of a Cu-click
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Articles

What is Click Chemistry? An Introduction

Explore click chemistry: efficient, high-yield reactions for drug discovery, bioconjugation, and green chemistry with simple conditions and wide applications.

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

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