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Chemischer Name: (S)-2-(Fmoc-amino)-5-(Boc-aminoxy)pentanoic acid // Synonyme: (S)-Fmoc-Hcan(Boc)-OH, Fmoc-L-Homocanaline(Boc)-OH, (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(((tert-butoxycarbonyl)amino)oxy)pentanoic acid, Fmoc-Hcan(Boc)-OH,Fmoc-(S)-Hcan(Boc)-OH, (N-a lpha-(9-Fluorenylmethyloxycarbonyl)-amino)-5-((t-b
Ab 175,00 €
L-homocanaline (HCan) represents a structural analogue of lysine, which contains a reactive alkyloxyamine side chain. The aminooxy group exhibits greater nucleophilicity than the corresponding primary amino group. It is therefore considered to react chemoselectively with carbonyl compounds by forming a kinetically stable oxime bond, which is more stable than an imine bond.
Chemoselectively adressable HCan building blocks in peptide synthesis: L-homocanaline derivatives; I. Lang, N. Donzé, P. Garrouste, P. Dumy, M. Mutter; J. Pept. Sci. 1998; 4: 72-80. https://doi.org/10.1002/(sici)1099-1387(199802)4:1<72::aid-psc130>3.0.co;2-g
Receptor-templated stapling of intrinsically disordered peptide ligands; C. M. Haney, and W. S. Horne; Org. Biomol. Chem. 2015; 13: 4183-4189. https://doi.org/10.1039/C5OB00269A
Synthetic derivatives of the SUMO consensus sequence provide a basis for improved substrate recognition; M. J. Leyva, Y. S. Kim, M. L. Peach, J. S. Schneekloth Jr.; Bioorg. Med. Chem. Lett. 2015; 25: 2146-2151. https://doi.org/10.1016/j.bmcl.2015.03.069
Site-specific cross-linking of proteins to DNA via a new biorthogonal approach employing oxime ligation; S. S. Pujari, Y. Zhang, S. Ji, M. D. Distefano, and N. Y. Tretyakova; Chem. Commun. 2018; 54: 6296-6299. https://doi.org/10.1039/C8CC01300D
