696773

Sigma-Aldrich

TentaGel TBTA

extent of labeling: 0.17 mmol/g loading

Synonym(s):
TBTA, Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine, polymer bound
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reaction type: solution phase peptide synthesis
reagent type: ligand
reaction type: click chemistry

Quality Level

extent of labeling

0.17 mmol/g loading

General description

Tentagel is a polystyrene resin. Tentagel resin acts as support for the heterogenization of click catalysts by their covalent and non-covalent immobilization. TentaGel TBTA is an efficient heterogeneous catalyst system, based on a tris(benzyltriazolyl) functionalized swellable Tentagel. TBTA (tris-(benzyltriazolylmethyl)amine) is a ligand frequently employed in click chemistry, as it protects and stabilizes the copper from oxidation, leading to a highly effective Huisgen copper-catalyzed azide-alkyne cycloaddition (CuAAC) catalyst.

Application

TentaGel TBTA may be used in the synthesis of artificial molecular machines which can pick up and assemble reactive groups in sequence by traveling along a track, useful for sequence-specific synthesis. It may be used in the synthesis of diimide and bipyridinium [2]rotaxanes in solution.
Solid supported ligand for enhancement of copper(I) catalyzed azide-alkyne cycloaddition reactions

Packaging

250 mg in amber glass bottle

Legal Information

TentaGel is a trademark of Rapp Polymere GmbH

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Mieke Lammens et al.
Chemical communications (Cambridge, England), 46(46), 8719-8721 (2010-08-21)
Tris-(benzyltriazolylmethyl)amine (TBTA) has been immobilized onto a styrenic monomer and subsequently copolymerized with styrene to afford catalytically active and reusable copolymers for the CuAAC reaction.
Guillaume De Bo et al.
Journal of the American Chemical Society, 136(15), 5811-5814 (2014-04-01)
We report on an improved strategy for the preparation of artificial molecular machines that can pick up and assemble reactive groups in sequence by traveling along a track. In the new approach a preformed rotaxane synthon is attached to the...
Non-Magnetic and Magnetic Supported Copper (I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry.
Megia-Fernandez A, et al.
Advanced Synthesis & Catalysis, 352(18), 3306-3320 (2010)
Hannah Wilson et al.
Organic & biomolecular chemistry, 11(13), 2105-2115 (2013-02-06)
Herein we describe the design and synthesis of a series of solid-tethered [2]rotaxanes utilising crown ether-naphthalene diimide or crown ether-bipyridinium host guest interactions. TentaGel polystyrene resins were initially modified in a two-stage procedure to azide functionalised beads before the target...
Mutian Jia et al.
Nature immunology, 21(7), 727-735 (2020-06-17)
Stimulator-of-interferon genes (STING) is vital for sensing cytosolic DNA and initiating innate immune responses against microbial infection and tumors. Redox homeostasis is the balance of oxidative and reducing reactions present in all living systems. Yet, how the intracellular redox state...

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