776173
5-Norbornene-2-acetic acid succinimidyl ester
97%
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Synonym(s):
2,5-Dioxopyrrolidin-1-yl 2-(bicyclo[2.2.1]hept-5-en-2-yl)acetate, 5-Norbornene-2-acetic acid NHS, Bicyclo[2.2.1]hept-5-ene-2-acetic acid N-hydroxysuccinimide ester, Bicyclo[2.2.1]hept-5-ene-2-acetic acid, 2,5-dioxo-1-pyrrolidinyl ester
Empirical Formula (Hill Notation):
C13H15NO4
CAS Number:
Molecular Weight:
249.26
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
assay
97%
form
solid
reaction suitability
reaction type: click chemistry
reagent type: linker
mp
115-120 °C
functional group
NHS ester
storage temp.
2-8°C
SMILES string
O=C(N1OC(C[C@H]2[C@@H]3C=C[C@@H](C3)C2)=O)CCC1=O
InChI
1S/C13H15NO4/c15-11-3-4-12(16)14(11)18-13(17)7-10-6-8-1-2-9(10)5-8/h1-2,8-10H,3-7H2
InChI key
AOGNOQQTUYLDKN-UHFFFAOYSA-N
Application
Succinimidyl ester functionalized norbornene. Succinimidyl ester group will react with amine containing compounds such as lysine residues on proteins/peptides. 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 reaction demonstrated to be useful in biological imaging applications.
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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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