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776173

Sigma-Aldrich

5-Norbornene-2-acetic acid succinimidyl ester

97%

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

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About This Item

Empirical Formula (Hill Notation):
C13H15NO4
CAS Number:
1234203-45-2
Molecular Weight:
249.26
UNSPSC Code:
12352106
PubChem Substance ID:
329767816
NACRES:
NA.22

Quality Level

100

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (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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