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3-Norbornene-L-serine

2-amino-3-{bicyclo[2.2.1]hept-5-en-2-yl}-3-hydroxypropanoic acid

Cat. No. Amount Price (EUR) Buy / Note
CLK-109-25 25 mg 165,00 Add to Basket/Quote Add to Notepad
CLK-109-100 4 x 25 mg 495,00 Add to Basket/Quote Add to Notepad
Structural formula of 3-Norbornene-L-serine (2-amino-3-{bicyclo[2.2.1]hept-5-en-2-yl}-3-hydroxypropanoic acid)
Structural formula of 3-Norbornene-L-serine

For research use only!

Shipping: shipped on blue ice

Storage Conditions: store at -20 °C
store dry

Shelf Life: 12 months after date of delivery

Molecular Formula: C10H15NO3

Molecular Weight: 197.23 g/mol

Exact Mass: 197.11 g/mol

Purity: ≥ 90 % (HPLC)

Form: white to off-white powder

Solubility: 80 % EtOH / 0.2M NH4OH up to 100 mM

Applications:
The norbornene-tetrazine click reaction is ideally suited for protein labeling in living cells.

Description:
The inverse-electron demand Diels-Alder reaction of a novel amino acid bearing a norbornene moiety 3-norbornene-L-serine with tetrazines is a bioorthogonal reaction that possesses exceptional kinetics (0.59 M-1s-1) and selectivity. Both the carboxylic acid and the amine functionalities on 3-norbornene-L-serine make it an ideal linker for the functionalization of diverse compounds by using N-hydroxysuccinimide ester and amine-carboxylic acid coupling system.

Note:
Prepare the stock solution of 3-norbornene-L-serine immediately before use.

Selected References:
Knall, A.C. et al.(2014) Kinetic studies of inverse electron demand Diels-Alder reactions (iEDDA) of norbornenes and 3,6-dipyridin-2-yl-1,2,4,5-tetrazine. Tetrahedron Lett 55(34):4763.
Lukesch, M. (2019) Novel amino acids bearing a norbornene moiety. U.S. Patent WO2019016354A1.