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Merck
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772828

Sigma-Aldrich

5-Norbornene-2-endo-acetic acid

同義詞:

Bicyclo[2.2.1]hept-5-en-2-ylacetic acid, Norbornene acetic acid

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About This Item

經驗公式(希爾表示法):
C9H12O2
CAS號碼:
分子量::
152.19
分類程式碼代碼:
12352106
PubChem物質ID:

形狀

liquid

品質等級

反應適用性

reaction type: click chemistry
reagent type: linker

折射率

n20/D 1.495

密度

1.124 g/mL at 25 °C

官能基

carboxylic acid

SMILES 字串

OC(CC1C[C@@H]2C=C[C@H]1C2)=O

InChI

1S/C9H12O2/c10-9(11)5-8-4-6-1-2-7(8)3-6/h1-2,6-8H,3-5H2,(H,10,11)/t6-,7+,8?/m1/s1

InChI 密鑰

HRVGJQMCNYJEHM-KVARREAHSA-N

應用

Carboxylic acid functionalized norbornene. Carboxylic acid can be used to modify amine containing compounds such as lysine residues on proteins/peptides via standard peptide coupling methods. Norbornene has been shown to react with 1,2,4,5-tetrazines in an inverse electron demand Diels-Alder cycloaddition reaction, which is a bioorthogonal click chemistry reaction demonstrated to be useful in biological imaging applications.

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訊號詞

Warning

危險聲明

危險分類

Acute Tox. 4 Oral - Aquatic Chronic 3

儲存類別代碼

10 - Combustible liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


分析證明 (COA)

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Hee-Sun Han et al.
Journal of the American Chemical Society, 132(23), 7838-7839 (2010-05-21)
We present a bioorthogonal and modular conjugation method for efficient coupling of organic dyes and biomolecules to quantum dots (QDs) using a norbornene-tetrazine cycloaddition. The use of noncoordinating functional groups combined with the rapid rate of the cycloaddition leads to
Neal K Devaraj et al.
Bioconjugate chemistry, 19(12), 2297-2299 (2008-12-05)
Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast

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