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BTTAA Sale

目录号 : GC30061

BTTAA是一种Cu(I)-稳定配体,能够很好地与泛素Glu18AzF反应。

BTTAA Chemical Structure

Cas No.:1334179-85-9

规格 价格 库存 购买数量
10mM (in 1mL Water)
¥2,800.00
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1mg
¥1,200.00
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5mg
¥3,000.00
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50mg
¥13,500.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

BTTAA is a Cu(I)-stabilizing ligand, whch performs potently with ubiquitin Glu18AzF.

BTTAA is a Cu(I)-stabilizing ligand. Using the Glu18AzF mutant of ubiquitin as a model system with C3-Tm3+ and C4-Tm3+, Cu-BTTAA performs significantly better as a catalyst than Cu-THPTA or Cu-TBTA. BTTAA proves to perform much better than THPTA (tris[(1-hydroxy-propyl-1H-1,2,3-triazol-4-yl)methyl]amine) or TBTA (tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine)[1].

[1]. Loh CT et al. Lanthanide tags for site-specific ligation to an unnatural amino acid and generation of pseudocontact shifts inproteins. Bioconjug Chem. 2013 Feb 20;24(2):260-8.

BTTAA 是一种稳定 Cu(I) 的配体,与泛素 Glu18AzF 一起有效发挥作用。

BTTAA 是一种稳定 Cu(I) 的配体。使用泛素的 Glu18AzF 突变体作为具有 C3-Tm3+ 和 C4-Tm3+ 的模型系统,Cu-BTTAA 作为催化剂的性能明显优于 Cu-THPTA 或 Cu-TBTA。 BTTAA 证明比 THPTA(三[(1-羟基丙基-1H-1,2,3-三唑-4-基)甲基]胺)或 TBTA(三[(1-苄基-1H-1, 2,3-三唑-4-基)甲基]胺)[1].

[1]. Loh CT 等人。用于与非天然氨基酸进行位点特异性连接并在蛋白质中产生假接触位移的镧系元素标签。生物结合化学。 2013 年 2 月 20 日;24(2):260-8。

Chemical Properties

Cas No. 1334179-85-9 SDF
Canonical SMILES O=C(O)CN1N=NC(CN(CC2=CN(C(C)(C)C)N=N2)CC3=CN(C(C)(C)C)N=N3)=C1
分子式 C19H30N10O2 分子量 430.51
溶解度 Water : 5 mg/mL (11.61 mM) 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.3228 mL 11.6141 mL 23.2283 mL
5 mM 0.4646 mL 2.3228 mL 4.6457 mL
10 mM 0.2323 mL 1.1614 mL 2.3228 mL
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Research Update

Lanthanide tags for site-specific ligation to an unnatural amino acid and generation of pseudocontact shifts in proteins

Bioconjug Chem.2013 Feb 20;24(2):260-8.PMID: 23294422DOI:10.1021/bc300631z

Pseudocontact shifts (PCS) from paramagnetic lanthanide ions present powerful long-range structural restraints for structural biology by NMR spectroscopy, but site-specific tagging of proteins with lanthanides remains a challenge, as most of the available lanthanide tags require proteins with single cysteine residues. We show that cyclen-based paramagnetic lanthanide tags can be attached to proteins in a site-specific manner by Cu(I)-catalyzed azide-alkyne cycloaddition to a genetically encoded p-azido-l-phenylalanine residue with a tether that proved sufficiently short and rigid for the observation of PCSs in several proteins. Despite the sterically demanding conditions associated with bulky tags and reactions close to the protein surface, ligation yields consistently above 50% and approaching 100% were obtained with the help of the Cu(I)-stabilizing ligand BTTAA. The yields were high independent of the presence of cysteine residues, thereby avoiding the need for cysteine mutations associated with conventional lanthanide-tagging strategies.

Copper-Triggered Bioorthogonal Cleavage Reactions for Reversible Protein and Cell Surface Modifications

J Am Chem Soc. 2019 Oct 30;141(43):17133-17141. PMID: 31580665DOI:10.1021/jacs.9b05833

Temporal and reversible control over protein and cell conjugations holds great potential for traceless release of antibody-drug conjugates (ADCs) on tumor sites as well as on-demand altering or removal of targeting elements on cell surface. We herein developed a bioorthogonal and traceless releasable reaction on proteins and intact cells to fulfill such purposes. A systematic survey of transition metals in catalyzing the bioorthogonal cleavage reactions revealed that copper complexes such as Cu(I)-BTTAA and dual-substituted propargyl (dsPra) or propargyloxycarbonyl (dsProc) moieties offered a bioorthogonal releasable pair for reversible blockage and rescue of primary amines and phenol alcohols on small molecule drugs, protein side chains, as well as intact cell surface. For proof-of-concept, we employed such Cu(I)-BTTAA/dsProc and Cu(I)-BTTAA/dsPra pairs as a "traceless linker" strategy to construct cleavable ADCs to unleash cytotoxic compounds on cancer cells in situ and as a "reversible modification" strategy for cell surface engineering. Furthermore, by coupling with the genetic code expansion strategy, we site-specifically modulated ligand-receptor interactions on live cell membranes. Together, our work expanded the transition-metal-mediated bioorthogonal cleavage tool kit from terminal decaging to internal-linker breakage, which offered a temporal and reversible conjugation strategy on therapeutic proteins and cells.