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H-L-Lys(Norbornene-methoxycarbonyl)-OH*HCl
Chemical name: N-epsilon-(norbornene-methoxycarbonyl)-L-lysine hydrochloride // Synonyms: N6-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)carbonyl)-L-lysine hydrochloride, H-Lys(norbornene-methoxycarbonyl)-OH*HCl
- Product code:HAA9235
- CAS No.:1378916-76-7 net
- Formula:C15H24N2O4*HCl
- Molecular weight:296.37*36.46 g/mol
- Purity :min. 95%
Starting at $468.75
description
One popular technique for the modification of proteins is based on the incorporation of genetically encoded non-natural amino acids by using biorthogonal tRNA/tRNA-synthetase pairs. This norbornene-derivatized lysine can be click-functionalized with azides partially under Cu(I) catalysis or with tetrazines in Diels-Alder reactions with inverse electron demand. Both wildtype and specifically mutated pyrrolysine synthetases (PyIRSs) are reported to load this noncanonical amino acid onto the cognate pyrrolysine tRNA.
This product is a mixture of two isomers.
references
Structural insights into incorporation of norbornene amino acids for click modification of proteins; S. Schneider, M. J. Gattner, M. Vrabel, V. Fluegel, V. Lopez-Carrillo, S. Prill, T. Carell; ChemBioChem 2013; 14(16): 2114-2118. https://doi.org/10.1002/cbic.201300435.
A need for speed: genetic encoding of rapid cycloaddition chemistries for protein labelling in living cells; M. J. Schmidt, D. Summerer; ChemBioChem 2012; 13(11): 1553-1557. https://doi.org/10.1002/cbic.201200321.
A genetically encoded norbornene amino acid for the mild and selective modification of proteins in a copper-free click reaction; E. Kaya, M. Vrabel, C. Deiml, S. Prill, V. S. Fluxa, T. Carell; Angew. Chem. Int. Ed. 2012; 51(18): 4466-4469. https://doi.org/10.1002/anie.201109252.
Amino Acids for Diels-Alder Reactions in Living Cells; T. Plass, S. Milles, C. Koehler, J. Szymansk, R. Mueller, M. Wiessler, C. Schultz, E. A. Lemke; Angew. Chem. Int. Ed. 2012; 51(17): 4166-4170. https://doi.org/10.1002/anie.201108231.
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