Chemistry and Physics of Lipids p. 43 - 50 (1995)
Update date:2022-08-16
Topics:
Alaiz, Manuel
Barragan, Santiago
The reaction of E-2-octenal and N2-(carbobenzyloxy)-L-lysine was investigated and the products analyzed to identify the components that produce a significant loss of lysine residues in the reaction of E-2-octenal and proteins. When the mixture of N2-(carbobenzyloxy)-L-lysine and E-2-octenal was incubated at pH 7.0 and 37 deg C for 24 h, seven products were isolated, and their structures are suggested to be E-2-octenoic acid (4), 4-butyl-E-2-E-4-E-6-dodecatrien-1-al (3), 6-ethyl-5-pentyl-1,3-cyclohexadiene (1), 3,8-dibutyl-1-(2'-butyl-4'-formyl-1'-E-3'-E-butadien-1'-yl) -5-pentyl-2,6-dihydronaftalene (2), 1-(N2-(carbobenzyloxy)-L-lysyl)-2-(1'-carboxymethyl)-4-pentylpyridinium betaine (6), 1-(N2-(carbobenzyloxy)-L-lysyl)-2-(3'-carboxy-2'-E-propen-1'-yl)-4-pentylpyridinium betaine (7) and bis(1-(N2-(carbobenzyloxy)-L-lysyl)-2-(3'-carboxy-2'-propen-1',2'-diyl)-4-pentylpyridinium betaine) (5). Plausible mechanisms for the formation of those compounds are proposed. Keywords: N2-(Carbobenzyloxy)-L-lysine; E-2-Octenal; Pyridinium salts; Reaction
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