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Azide-Phosphine (Staudinger Ligation) Reagent Guide

Guide to azide- and phosphine-activated reagents for biomolecular conjugation, metabolic labeling, detection and affinity purification.

Thermo Scientific Azide and Phosphine Reagents are chemical or metabolic labeling reagents for in vivo or in vitro chemoselective ligation of proteins and post-translational modification moieties. The crosslinking strategy is called Staudinger ligation and makes possible a variety of specific detection, tagging and affinity purification approaches for studying cellular responses and pathways.

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Overview of Staudinger ligation for biomolecular conjugation.

Overview of Staudinger ligation (azide-phosphine conjugation). Azide and phosphine reagent pairs enable specific crosslinking and labeling of biomolecules to facilitate cellular pathway analysis. When combined, phosphine-activated compounds conjugate with high specificity to azide-tagged molecules, resulting in stable covalent attachment of "A" and "B" molecules.

Detection of metabolically incorported azido-mannosamine with Thermo Scientific DyLight 650-Phosphine. HK-2 cells were incubated with N-azidoacetylmannosamine and the live cells were probed with azide-reactive DyLight 650-Phosphine (blue). Nuclei were counterstained with Hoechst33342 (red).

Highlights:

Easy-to-use – two-component reaction with no additional accessory reagents required
Chemoselective – specific reactivity of azide and phosphine minimizes off-target effects and produces very low background
Bioorthogonal – azido sugars are naturally incorporated without affecting biological activity
Copper-free – unlike other chemoselective ligation chemistries, Staudinger ligation is non-toxic to live cells and does not oxidize amino acid side chains or post-translational modifications

Features	Benefits
Chemoselective reactivity	Virtually no side reactions with other functional groups Detect and enrich without contamination Accurate and representative biological observations
Compatible with bioorthogonal metabolic labeling	Terminal azido functional groups not found in living systems Azido derivatives of biological molecules are well tolerated
High reaction efficiency	Close to 100% reaction efficiency in chemical model systems
Ease of use	Two-reagent system is easier to use and troubleshoot than alternative copper-catalyzed click chemistry (5 different reagents)
Biological-sample compatiibility	Reactions occur in aqueous solutions at physiological pH with no known side reactions with buffers/detergents No risk for toxicity and protein oxidation because of the absence of Cu(I)
Allows probe switching	Azido-labeled molecules can be derivatized with wide variety of phosphine probes

Learn More...

Metabolic Labeling for Chemoselective Ligation – description and examples of chemoselective ligation and bioorthogonal in vivo labeling strategies
Staudinger Ligation Reaction Chemistry – diagram and more detailed description of the azide-phosphine reaction chemistry
Superiority of Azide-Phosphine Chemistry – experimental data comparing Staudinger ligation to azide-alkyne "click" chemistry
Protein Methods Library – links to articles about other crosslinking and labeling techniques

Azide-Phosphine Products:

Quick-Link Product Table:

Phosphine (P3) Products	Azide (N3) Products
Phosphine Labeling Reagents	Chemical Azide Labeling Reagents
Amine-reactive: • NHS-Phosphine • Sulfo-NHS-Phosphine	Amine-reactive: • NHS-Azide • NHS-PEG4-Azide • NHS-PEG12-Azide
Phosphine-Activated Reagents	Bioorthogonal Azide Labeling Compounds
Biotinylated: • Biotin-PEG3-Phosphine Fluorescent: • DyLight 488-Phosphine • DyLight 550-Phosphine • DyLight 650-Phosphine	Sugars: • GlcNAz (azido-acetylglucosamine) • GalNAz (azido-acetylgalactosamine) • ManNAz (azido-acetylmannosamine)

Product List: