Theoretical Study on Hydrophobicity of Amino Acids by the Solvation Free Energy Density Model

Junhyoung Kim, Ky Youb Nam, Kwang Hwi Cho, Seung Hoon Choi, Jae Sung Noh, Kyoung Tai No

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Abstract

In order to characterize the hydrophobic parameters of N-acetyl amino acid amides in 1-octanol/water, a theoretical calculation was carried out using a solvation free energy density model. The hydrophobicity parameters of the molecules are obtained with the consideration of the solvation free energy over the solvent volume surrounding the solute, using a grid model. Our method can account for the solvent accessible surface area of the molecules according to conformational variations. Through a comparison of the hydrophobicity of our calculation and that of other experimental/theoretical works, the solvation free energy density model is proven to be a useful tool for the evaluation of the hydrophobicity of amino acids and peptides. In order to evaluate the solvation free energy density model as a method of calculating the activity of drugs using the hydrophobicity of its building blocks, the contracture of Bradykinin potentiating pentapeptide was also predicted from the hydrophobicity of each residue. The solvation free energy density model can be used to employ descriptors for the prediction of peptide activities in drug discovery, as well as to calculate the hydrophobicity of amino acids.

Original languageEnglish
Pages (from-to)1742-1750
Number of pages9
JournalBulletin of the Korean Chemical Society
Volume24
Issue number12
DOIs
Publication statusPublished - 2003 Dec 20

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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