Skip to main content
. 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 9.

Calculated at the ub3lyp/6-311+g(d,p) level of theory the nucleophilicity indexes, ω−, of basic amino acids histidine, lysine, arginine, and model Ala-His-Ala tripeptide in their reactions with electrophilic derivatives of cyclopentonone in different ionization states (indicated in round brackets ). The nucleophilicity indexes of nonconjugated epoxide are shown for comparison.

Electrophile ω− (eV)
His
(0)		 His
(+1)		 Ala-His-Ala
(0)		 Ala-His-Ala
(+1)		 Lys
(0)		 Lys
(+1)		 Arg
(0)		 Arg
(+1)
15d-PGJ2 0.028 0.844 0.028 0.45 0.037 0.608 0.036 0.488
Δ12-PGJ2 0.0188 0.78 0.0189 0.414 0.026 0.553 0.025 0.459
PGA2 0.02 0.737 0.02 0.39 0.028 0.518 0.027 0.433
PGJ2 0.0112 0.845 0.0113 0.462 0.017 0.609 0.0163 0.508
Cyclo-
pentene		 0.0158 0.737 0.0158 0.39 0.022 0.518 0.021 0.438
Epoxide 0.000003 0.63 0.000003 0.35 0.0003 0.44 0.00022 0.411