Reactivity of a Morita–Baylis–Hillman Adduct Derivative Bearing a Triphenylamine Moiety with Lysine Models

Abstract

The reactivity of Morita‐Baylis‐Hillman Adduct (MBHA) derivative 7 was studied with different primary amine derivatives such as n‐butylamine, Na‐acetyl‐L‐lysine methyl ester, and a poly‐(L‐lysine) derivative as lysine models to obtain information about the possible reactions in complex protein environments. MBHA derivative 7 reacted with n‐butylamine or Na‐acetyl‐L‐lysine methyl ester producing monoadducts 9a or 9c, which showed bright emission features in the green region at 526‐535 nm with photoluminescence quantum yield values in solutions of 73% and 51%, respectively. Based on these results, MBHA derivative 7 can be considered an interesting new fluorogenic probe potentially useful in the labelling of basic amino acid residues. Furthermore, similar to other MBHA derivatives, compound 7 showed the tendency to produce diadducts especially in polar solvents system where specific interactions between the extended aromatic moieties may play a major role.