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MilliporeSigma

906328

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

Key Documents

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assay

≥95%

form

solid

reaction suitability

reaction type: click chemistry

availability

available only in USA

storage temp.

2-8°C

SMILES string

[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)

InChI key

MGQYHUDOWOGSQI-UHFFFAOYSA-N

Related Categories

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

pictograms

Flame
GHS02

signalword

Danger

hcodes

H242

Hazard Classifications

Self-react. C

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ3027
MKCT2342
MKCS4316
MKCQ0031
MKCM6976

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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
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
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
Christen Besanceney-Webler et al.
Bioorganic & medicinal chemistry letters, 21(17), 4989-4992 (2011-06-17)
Members of the Bacteroidales order are among the most abundant gram-negative bacteria of the human colonic microbiota. These species decorate their cell-surface glycoproteins with fucosylated glycans, which are believed to play important roles in host intestinal colonization. Currently, there is
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
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