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. Author manuscript; available in PMC: 2014 Aug 19.
Published in final edited form as: Mass Spectrom Rev. 2014 May-Jun;33(3):157–182. doi: 10.1002/mas.21389

Table 4.

Calculated at the ub3lyp/6-311+g(d,p) level of theory the nucleophilicity indexes, ω−, of cysteine and model Ala-Cys-Ala tripeptide in their reactions with electrophilic α,β-unsaturated carbonyl compounds in different ionization states (indicated in round brackets).

Electrophile ω− (eV)
Cys
(−1)		 Cys
(0)		 Ala-Cys-Ala
(−1)		 Ala-Cys-Ala
(0)
DODE 2.56 0.106 1.965 0.145
ONE 2.55 0.099 1.955 0.137
Acrolein 1.721 0.0306 1.262 0.051
HNE (cis) 1.726 0.024 1.264 0.042
MDA[1] 1.605 0.0284 1.17 0.047
HHE 1.62 0.019 1.177 0.035
HNE (trans) 1.61 0.018 1.17 0.034
Crotonaldehyde 1.532 0.0125 1.106 0.026
MDA[2] 1.483 0.0062 1.065 0.0166