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Staudinger Reagent Selection Guide

Choose an appropriate reagent for metabolic labeling and chemoselective ligation.

Staudinger azide-phosphine reagent selection guideThermo 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 azide-phosphine 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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Metabolic Labeling Strategies

Staudinger Reaction Chemistry

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Metabolic Labeling Reagents

Chemoselective Crosslinking Reagents

Description

Overview of chemoselective ligation for biomolecular conjugation.
Staudinger chemoselective ligation as a strategy for metabolic labeling. Phosphine-activated reagents (e.g., fluorescent dyes) will specifically conjugate to azide-labeled biomolecules to allow specific detection, purification and measurement.

 

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

 

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Metabolic Labeling Strategies

Staudinger Reaction Chemistry

 

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Bioconjugate Techniques, Greg Hermanson
Bioconjugate Techniques
(book)

Highlights, Features and Benefits

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

Quick-link Table of Products

  Azide (N3) Products Phosphine (P3) Products
Reagents for
chemical activation
and conjugation:
Crosslinking
Amine-reactive:
    • NHS-Azide
    • NHS-PEG4-Azide
 
Amine-reactive:
    • NHS-Phosphine
 

Reagents for
metabolic labeling
and detection:
Labeling

Sugars:
    • GlcNAz (azido-acetylglucosamine)
    • GalNAz (azido-acetylgalactosamine)
    • ManNAz (azido-acetylmannosamine)
Biotinylated:
    • Biotin-PEG3-Phosphine

Fluorescent:
    • DyLight 488-Phosphine
    • DyLight 550-Phosphine
    • DyLight 650-Phosphine


Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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