CAS 1341215-17-5
BTTP
About This Compound
Triazole-containing ligands are specialized additives designed to accelerate and stabilize Cu(I)-catalyzed click reactions. THPTA, BTTAA, and related polytriazole ligands coordinate Cu(I) ions, preventing oxidative degradation while maintaining catalytic activity. These ligands are essential for performing CuAAC in aqueous media and biological systems, where unprotected Cu(I) would rapidly generate reactive oxygen species that damage proteins and nucleic acids.
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CAS Registry1341215-17-5
Literature Refs33 references
Synthesis Routes
Showing 2 of 2 available routes, sorted by yield.
Route 1
CAS 1341215-17-5
C20H34N10O
Route 2
CAS 72320-38-8
C3H7N3O
CAS 1257633-68-3
C17H27N7
Related Compounds
Other Triazole Ligands & Catalysts in our catalog:
Frequently Asked Questions
Why do I need a triazole ligand for CuAAC in biological systems?
Cu(I) ions in aqueous solution rapidly react with dissolved oxygen to produce Cu(II) and reactive oxygen species (ROS), which oxidatively damage proteins, DNA, and lipids. Triazole ligands like THPTA and BTTAA tightly chelate Cu(I), shielding it from oxygen while maintaining its catalytic activity. This reduces biomolecular damage by >90% compared to ligand-free CuAAC.
What is the optimal ligand-to-copper ratio?
For THPTA, a 2:1 or 3:1 ligand:Cu ratio is standard (e.g., 1.8 mM THPTA with 0.9 mM CuSO₄). For BTTAA, a 3:1 ratio is recommended. Excess ligand ensures complete Cu(I) coordination but very high concentrations may inhibit the reaction by over-stabilizing Cu(I) and reducing its reactivity with the azide.
Can I use THPTA for in vivo click chemistry?
THPTA is suitable for cell-surface labeling and extracellular applications but has limited cell permeability. For intracellular CuAAC, BTTAA offers better biocompatibility, though copper-free methods (SPAAC, IEDDA) are generally preferred for live-cell applications. THPTA has been successfully used for zebrafish embryo labeling at low Cu concentrations.
How should I store triazole ligand solutions?
Stock solutions of THPTA or BTTAA (10–100 mM in DMSO or water) can be stored at −20 °C for several months. Avoid repeated freeze-thaw cycles. Working solutions (1–10 mM) should be prepared fresh or stored at 4 °C for up to one week. The ligands are stable at room temperature as solids.
Last updated: July 27, 2026