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NHS-Azide Staudinger Ligation Reagents


Amine-reactive azide labeling reagents for azide-phosphine chemoselective ligation.

NHS-Azide Staudinger Ligation Reagents

Thermo Scientific NHS-Azide reagents are amine-reactive compounds that can be used to derivatize primary amines of proteins or amine-coated polymer surfaces for ligation to phosphine-modified molecules.

These NHS-ester compounds react to form covalent bonds with primary amines (e.g., side chain of lysine residues or aminosilane-coated surfaces). The azide (N3) group reacts with phosphine-labeled molecules by a mechanism known as Staudinger chemistry, enabling efficient and specific conjugation of derivatized molecules in biological samples. In combination with different phosphine-activated compounds, these NHS-Azide reagents facilitate a variety of labeling and crosslinking experimental strategies for investigating protein interactions and cellular pathways.

Highlights:

  • Soluble – reagents easily dissolve in water-miscible solvents for subsequent dilution in aqueous reaction mixtures with cell lysates and other biological samples
  • Compatible – reaction chemistry occurs effectively in simple buffer conditions; requires no accessory reagents such as copper or reducing agents
  • Specific – NHS esters are specific for covalent attachment to primary amines (side chain of lysine or N-terminus of polypeptides)
  • Chemoselective – azide and phosphine groups do not react or interfere with components of biological samples (bioorthogonal) but conjugate to one another with high efficiency
  • Pegylated – choose the very short NHS-Azide or a variety whose spacer arm contains a 4-unit polyethylene glycol (PEG) group for increased solubility and reach

Product Details:

NHS-Azide NHS-PEG4-Azide
Chemical structures of NHS-Azide Reagents. These reagents label proteins and molecules that contain primary amines (e.g., side-chain of lysine) via the NHS Ester Reaction Chemistry. Labeled molecules will contain an azide group (N3), which can be conjugated and detected using phosphine-activated probes via the Staudinger Ligation Reaction Chemistry.

Properties of NHS-Azide reagents. These compounds are identical except for the their overall length as a result of different numbers of polyethylene glycol groups (PEG units).
  NHS-Azide NHS-PEG4-Azide
Chemical formula C6H6N4O4 C15H24N4O8
Molecular weight 198.14 388.37
Spacer arm length 2.5 angstroms 18.9 angstroms
Form white to off-white powder colorless to pale yellow liquid
SMILES structures O=C(ON1C(CCC1=O)=O)CN=[N+]=[N-]
O=C(CCC1=O)N1OC(CCOCCOCCOCCOCCN=[N+]=[N-])=O
Storage conditions -20°C with desiccant, protect from moisture and light, use only fresh solutions
Reactive groups N-hydroxysuccinimide ester, reacts with primary amines at pH 7.0-9.0;
Azide, reacts with phosphine groups

Related Resources:

Azide-Phosphine Reagent Guide
Review of Metabolic Labeling for Chemoselective Ligation
Review of Staudinger Ligation Reaction Chemistry
Superiority of Azide-Phosphine Chemistry

Related Products:

Azide-Sugars for Metabolic Labeling and Detection
NHS-Phosphine Staudinger Ligation Reagents
Phosphine-activated DyLight Fluors
Biotin-PEG3-Phosphine


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
26130 NHS-PEG4-Azide
Formulation: Tetraethyleneglycol functionalized with succinimidyl and azido ends; liquid
Sufficient For: 257mL of typical 1X (1mM) reaction solution, or approx. 50 uses at 2mg reagent per use
100mg Product Instructions for product #26130 NHS-PEG4-Azide MSDS for product #26130 NHS-PEG4-Azide Certificate of Analysis for product #26130 NHS-PEG4-Azide $242.00

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88902 NHS-Azide
Formulation: Ethane functionalized with succinimidyl and azido ends; solid
Sufficient For: 50mL of typical 1X (1mM) reaction solution, or approx. 5 uses at 2mg reagent per use
10mg Product Instructions for product #88902 NHS-Azide MSDS for product #88902 NHS-Azide $205.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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