772828
5-Norbornene-2-endo-acetic acid
Synonym(s):
Bicyclo[2.2.1]hept-5-en-2-ylacetic acid, Norbornene acetic acid
form
liquid
reaction suitability
reaction type: click chemistry
reagent type: linker
refractive index
n20/D 1.495
density
1.124 g/mL at 25 °C
functional group
carboxylic acid
SMILES string
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
Application
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Chronic 3
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(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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