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Cyclization Effect on pKa of the Side Chain of Aspartic Acid in Dipeptides: A DFT Study

[ Vol. 17 , Issue. 5 ]


Mohsen Sargolzaei* and Majid Namayandeh Jorabchi   Pages 381 - 387 ( 7 )


Cyclic dipeptides are very important compounds that have a wide range of applications in pharmaceutical chemistry and life sciences. In the current work, the acidity of the side chain of aspartic acid was calculated for various linear and a cyclic dipeptide. pKa values were derived using the thermodynamics cycle and DFT/B3LYP approach. The obtained pKa values show strong acidity for cyclic with respect to linear dipeptides. We found an intramolecular hydrogen bond in cyclic dipeptide structure, which can be used to justify the increasing acidity of the side chain of Asp as compared to linear structures.


Density functional theory, dipeptide, pKa, thermodynamics cycle, cyclic dipeptide, aspartic acid.


Department of Chemistry, Shahrood University of Technology, Shahrood, University of Rostock, Institute of Chemistry, Physical and Theoretical Chemistry, Albert-Einstein-Stra├če 21, 18059 Rostock

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