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Merck
CN

772828

Sigma-Aldrich

5-Norbornene-2-endo-acetic acid

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别名:
Bicyclo[2.2.1]hept-5-en-2-ylacetic acid, Norbornene acetic acid
经验公式(希尔记法):
C9H12O2
CAS号:
分子量:
152.19
UNSPSC代码:
12352106
PubChem化学物质编号:
NACRES:
NA.22

形式

liquid

质量水平

反应适用性

reaction type: click chemistry
reagent type: linker

折射率

n20/D 1.495

密度

1.124 g/mL at 25 °C

官能团

carboxylic acid

SMILES字符串

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 key

HRVGJQMCNYJEHM-KVARREAHSA-N

应用

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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危险声明

预防措施声明

危险分类

Acute Tox. 4 Oral - Aquatic Chronic 3

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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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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