943800
1-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-2,5-pyrrolidinedione
≥95%
Synonym(s):
(Norbornene-2-yl)-N-hydroxysuccinimidylcarbonate, Bicyclo[2.2.1]hept-5-en-2-yl (2,5-dioxo-1-pyrrolidinyl) ester, 1-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-2,5-pyrrolidinedione, Carbonic acid, Norbornene-NHS
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Quality Level
assay
≥95%
form
solid
storage condition
protect from light
color
off-white
storage temp.
−20°C
SMILES string
O=C(ON1C(=O)CCC1=O)OC2CC3C=CC2C3
InChI
1S/C12H13NO5/c14-10-3-4-11(15)13(10)18-12(16)17-9-6-7-1-2-8(9)5-7/h1-2,7-9H,3-6H2
InChI key
UFPOHRPAWSDIKK-UHFFFAOYSA-N
General description
Norbornene-NHS is a norbornene-based NHS-carbonate reagent. It combines a norbornene moiety (a strained bicyclic alkene) with an N-hydroxysuccinimide (NHS) carbonate functional group. As such, it acts as an activated ester that can be used to functionalize primary amines or other nucleophiles, introducing a norbornene handle often used in bioorthogonal / click chemistry, especially in tetrazine / inverse-electron-demand Diels–Alder (IEDDA) reactions.
Application
- Bioorthogonal labeling / click chemistry: As a reagent to install norbornene handles on biomolecules, enabling subsequent reaction with tetrazines (copper-free IEDDA)
- Protein / Antibody conjugation: To functionalize amine sites on proteins / antibodies with a norbornene handle for downstream conjugation
- Probe development / imaging: For preparing labeled biomolecules or imaging probes via bioorthogonal chemistry
- Linker chemistry: As part of molecular constructs needing a controllable click handle
Features and Benefits
- Norbornene moiety - Provides a strained alkene for fast IEDDA (“bioorthogonal”) reactions with tetrazines, useful in labeling / conjugation workflows
- Activated NHS carbonate - Readily reacts with amines (e.g. lysines, amino linkers) to install the norbornene handle
- Versatile in conjugation - Useful in protein / antibody labeling, probe design, site-specific modification
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| 943800-100MG | 04065273705324 |