
BTTAA ligand | CAS 1334179-85-9
| Catalog Number | R17-0001 |
| Category | Click Chemistry Ligands and Catalysts |
| Molecular Formula | C19H30N10O2 |
| Molecular Weight | 430.52 |
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Product Introduction
BTTAA is the newest generation of water-soluble ligands for Cu(I)-catalyzed azide-alkyne click chemistry reactions (CuAAC).
Chemical Information
Application
Chemical Information
| Synonyms | BTTAA; (4-{[bis-(1-tert-butyl-1H-[1,2,3]triazol-4-ylmethyl)-amino]-methyl}-[1,2,3]triazol-1-yl)-acetic acid |
| IUPAC Name | 2-[4-[[bis[(1-tert-butyltriazol-4-yl)methyl]amino]methyl]triazol-1-yl]acetic acid |
| SMILES | CC(C)(C)N1C=C(N=N1)CN(CC2=CN(N=N2)CC(=O)O)CC3=CN(N=N3)C(C)(C)C |
| InChI | InChI=1S/C19H30N10O2/c1-18(2,3)28-11-15(21-24-28)8-26(7-14-10-27(23-20-14)13-17(30)31)9-16-12-29(25-22-16)19(4,5)6/h10-12H,7-9,13H2,1-6H3,(H,30,31) |
| InChIKey | MGQYHUDOWOGSQI-UHFFFAOYSA-N |
| Solubility | Soluble in water, DMSO, DMF, MeOH |
| Appearance | Off-white to Grey Solid |
Application
BTTAA ligand is a bidentate tris(triazolylmethyl)amine ligand commonly used to accelerate copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) by stabilizing the active Cu(I) species. Its coordination-friendly, click-optimized structure makes it particularly relevant for workflows that require fast labeling under mild conditions, including sensitive biomolecule conjugation and high-throughput probe preparation. As a widely adopted additive, BTTAA ligand is frequently selected to improve labeling efficiency and reproducibility across diverse substrates and material surfaces.
1. CuAAC Probe Labeling
BTTAA ligand is used in CuAAC-based probe synthesis to support efficient conversion of azide and alkyne partners into stable triazole-linked products. Researchers rely on BTTAA ligand when preparing fluorescent tags, affinity handles, and detection reagents for analytical chemistry and chemical biology, where consistent labeling across different biomolecular scaffolds is important. In practical reagent development, the ligand helps mitigate variability caused by substrate-dependent copper speciation, enabling more robust assembly of labeled libraries for downstream imaging, binding assays, and method development.
2. Biomolecule Conjugation Workflows
BTTAA ligand is commonly incorporated into bioconjugation protocols to generate triazole-linked conjugates from azide-functional biomolecules and alkyne-bearing partners. Molecular biology groups and chemical biology laboratories use BTTAA ligand to streamline labeling of proteins, peptides, glycans, and nucleic-acid derivatives where reaction conditions must remain compatible with complex, functional biomolecular environments. The ligand’s role as a Cu(I)-stabilizing additive supports reproducible conjugation outcomes, which is valuable for building standardized reagent sets for mechanistic studies, target engagement tools, and platform development.
3. Surface and Material Functionalization
BTTAA ligand is applied to surface chemistry and materials functionalization strategies that use CuAAC to attach bioactive or analytical moieties to solid supports. Materials scientists and diagnostic reagent developers use BTTAA ligand to promote efficient coupling on polymer surfaces, hydrogel matrices, and microfabricated platforms where copper access and local environment can influence labeling yield. By improving the reliability of CuAAC under heterogeneous conditions, BTTAA ligand supports the preparation of functional coatings, affinity surfaces, and immobilized probe arrays used in binding studies and analytical workflows.
4. Molecular Imaging Reagent Assembly
BTTAA ligand is frequently used during the construction of imaging-oriented click probes that require triazole-linked architectures for stable conjugate formation. Imaging chemistry teams and molecular imaging researchers incorporate BTTAA ligand into labeling pipelines to assemble conjugates that combine targeting motifs with reporter groups such as fluorophores or other detectable tags. Practical probe development often depends on consistent CuAAC performance across multiple functional components, and BTTAA ligand is selected to support dependable assembly of imaging reagent candidates for screening and characterization workflows.
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