Citation: Ming Liang Ma, Xiao Yan Li, Ke Wen, Yahu A. Liu. 5-Hexylidene-4-propylamino-1,5-dihydroimidazol-2-one formed from Cu-catalyzed oxidation with implication for the structure of a His-Lys cross-link[J]. Chinese Chemical Letters, ;2007, 18(9): 1025-1028. doi: 10.1016/j.cclet.2007.06.025 shu

5-Hexylidene-4-propylamino-1,5-dihydroimidazol-2-one formed from Cu-catalyzed oxidation with implication for the structure of a His-Lys cross-link

a Key Laboratory of Brain Functional Genomics, MOE & STCSM, Shanghai Institute of Brain Functional Genomics, East China Normal University, Shanghai 200062, China;
b Medicinal Chemistry, ChemBridge Research Laboratories Inc., San Diego, CA 92127, USA

Received Date: 9 April 2007

Fund Project: This work was supported by grants from Ministry of Science and Technology of China (973 Project,No.2003CB716600),Ministry of Education (No.106078),and Shanghai Commission for Science and Technology (No.06Pj14034,06DZ19002).

Cu-catalyzed oxidation of 5-hexyl-1, 3-dihydroimidazo-2-one (1) in the presence of propylamine, as surrogates for the oxidized His side chain and Lys side chain, was investigated. 5-Hexylidene-4-propylamino-1, 5-dihydroimidazol-2-one (2), a model His-Lys cross-link product, was isolated and structurally characterized by NMR and mass spectrometry.
- His-Lys cross-link,
- Metal-catalyzed protein oxidation,
- Oxidative stress
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