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906328

Sigma-Aldrich

BTTAA

≥95%

Synonyme(s) :

2-(4-((Bis((1-(tert-butyl)-1H-1,2,3-triazol-4-yl)methyl)amino)methyl)-1H-1,2,3-triazol-1-yl)acetic acid, Copper click-chemistry ligand, Water-soluble CuAAC ligand

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About This Item

Formule empirique (notation de Hill) :
C19H30N10O2
Numéro CAS:
1334179-85-9
Poids moléculaire :
430.51
Numéro MDL:
MFCD29918287
Code UNSPSC :
12352200

Essai

≥95%

Forme

solid

Capacité de réaction

reaction type: click chemistry

Disponibilité

available only in USA

Température de stockage

2-8°C

Chaîne SMILES 

[n]1(nnc(c1)CN(Cc3nn[n](c3)C(C)(C)C)Cc2nn[n](c2)CC(=O)O)C(C)(C)C

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)

Clé InChI

MGQYHUDOWOGSQI-UHFFFAOYSA-N

Application

BTTAA is a next-generation, water-soluble ligand for the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) that dramatically accelerates reaction rates and suppresses cell cytotoxicity. The biocompatibility and fast kinetics of BTTAA are advancements from water-insoluble TBTA and are desirable for bio conjugation in diverse chemical biology experiments.

Autres remarques

Biocompatible click chemistry enabled compartment-specific pH measurement inside E. coli

Fast, cell-compatible click chemistry with copper-chelating azides for biomolecular labeling

Metabolic labeling of fucosylated glycoproteins in Bacteroidales species

Increasing the Efficacy of Bioorthogonal Click Reactions for Bioconjugation: A Comparative Study

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Flame
GHS02

Mention d'avertissement

Danger

Mentions de danger

H242

Classification des risques

Self-react. C

Code de la classe de stockage

5.2 - Organic peroxides and self-reacting hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
MKCT2342
MKCS4316
MKCQ0031
MKCM6976
MKCM1711

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Maiyun Yang et al.
Angewandte Chemie (International ed. in English), 51(31), 7674-7679 (2012-07-06)
Live-cell pH measurements: An environment-sensitive fluorophore (green) was site-specifically introduced on HdeA, an acid-resistant chaperone showing pH-mediated conformational changes under low pH conditions. A survey of the attachment sites led to the discovery of one position on HdeA at which
Yong Liang et al.
Analytical chemistry, 86(8), 3688-3692 (2014-03-25)
P450 3A4 (CYP3A4) is one of the most important isoforms in the human cytochrome P450 superfamily. It was used as an example in this proof-of-concept study in order to demonstrate an activity-based labeling and then click chemistry (CC) mediated element-tagging
Yinliang Yang et al.
Molecules (Basel, Switzerland), 18(10), 12599-12608 (2013-10-16)
Activity-based protein profiling uses chemical probes that covalently attach to active enzyme targets. Probes with conventional tags have disadvantages, such as limited cell permeability or steric hindrance around the reactive group. A tandem labeling strategy with click chemistry is now
Junfeng Chen et al.
Journal of the American Chemical Society, 140(42), 13695-13702 (2018-09-08)
A major challenge in performing reactions in biological systems is the requirement for low substrate concentrations, often in the micromolar range. We report that copper cross-linked single-chain nanoparticles (SCNPs) are able to significantly increase the efficiency of copper(I)-catalyzed alkyne-azide cycloaddition
Zhiling Zhu et al.
Catalysis science & technology, 7(12), 2474-2485 (2017-11-14)
Ancillary ligands, especially the tripodal ligands such as tris(triazolylmethyl)amines, have been widely used to accelerate the Cu-catalyzed azide-alkyne cycloaddition (CuAAC, a "click" reaction). However, the relationship between the activity of these Cu(I) complexes and their stability against air oxidation and
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