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906328

Sigma-Aldrich

BTTAA

≥95%

Synonym(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

Empirical Formula (Hill Notation):
C19H30N10O2
CAS Number:
1334179-85-9
Molecular Weight:
430.51
MDL number:
MFCD29918287
UNSPSC Code:
12352200

Assay

≥95%

form

solid

reaction suitability

reaction type: click chemistry

availability

available only in USA

storage temp.

2-8°C

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.

Other Notes

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

related product

Product No.
Description
Pricing

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H242

Hazard Classifications

Self-react. C

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

906328-BULK:
906328-100MG:
906328-500MG:
906328-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fast, cell-compatible click chemistry with copper-chelating azides for biomolecular labeling.
Chayasith Uttamapinant et al.
Angewandte Chemie (International ed. in English), 51(24), 5852-5856 (2012-05-05)
Yongxian Xu et al.
Angewandte Chemie (International ed. in English), 57(15), 3949-3953 (2018-02-14)
Membrane voltage is an important biophysical signal that underlies intercellular electrical communications. A fluorescent voltage indicator is presented that enables the investigation of electrical signaling at high spatial resolution. The method is built upon the site-specific modification of microbial rhodopsin
Samra Obeid et al.
Chemical communications (Cambridge, England), 48(67), 8320-8322 (2012-07-07)
Modified nucleotides play a paramount role in many cutting-edge biomolecular techniques. The present structural study highlights the plasticity and flexibility of the active site of a DNA polymerase while incorporating non-polar "Click-able" nucleotide analogs and emphasizes new insights into rational
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
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
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