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重要文件

761982

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-alcohol

for Copper-free Click Chemistry

同義詞:

Polyethylene glycol, DBCO-PEG4-OH

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About This Item

經驗公式(希爾表示法):
C29H36N2O6
分子量::
508.61
分類程式碼代碼:
51171641
PubChem物質ID:
NACRES:
NA.22
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品質等級

形狀

solid

反應適用性

reaction type: click chemistry
reagent type: linker

mp

50-60 °C

官能基

hydroxyl

儲存溫度

−20°C

SMILES 字串

O=C(CCCCC(NCCOCCOCCOCCOCCO)=O)N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3

InChI

1S/C29H36N2O6/c32-16-18-36-20-22-37-21-19-35-17-15-30-28(33)11-5-6-12-29(34)31-23-26-9-2-1-7-24(26)13-14-25-8-3-4-10-27(25)31/h1-4,7-10,32H,5-6,11-12,15-23H2,(H,30,33)

InChI 密鑰

ZZXWONCQAFVJHM-UHFFFAOYSA-N

應用

Alcohol functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage. The PEG spacer adds hydrophilicity to the product to decrease aggregation.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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Nicholas J Agard et al.
ACS chemical biology, 1(10), 644-648 (2006-12-19)
Detection of metabolites and post-translational modifications can be achieved using the azide as a bioorthogonal chemical reporter. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly
Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions.
Xinghai Ning et al.
Angewandte Chemie (International ed. in English), 47(12), 2253-2255 (2008-02-16)
John C Jewett et al.
Journal of the American Chemical Society, 132(11), 3688-3690 (2010-03-02)
Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole
Jeremy M Baskin et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(43), 16793-16797 (2007-10-19)
Dynamic imaging of proteins in live cells is routinely performed by using genetically encoded reporters, an approach that cannot be extended to other classes of biomolecules such as glycans and lipids. Here, we report a Cu-free variant of click chemistry

文章

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

無銅單鍵化學是單鍵化學的另一種方法,它以較低的活化門檻進行,並且不含具有細胞毒性的過渡金屬催化劑。

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