Abstract
The distribution coefficients of free α-amino acids have been measured around their isoelectric value by centrifugal partition chromatography (CPC), allowing the determination of the partition coefficient (log P) of the amino acids in their zwitterionic form. Good correlations with published distribution coefficients of amino acid derivatives allowed log P values to be calculated for the five amino acids (Arg, Asn, Asp, Glu, Lys) whose high polarity prevented direct measurements by CPC. The log P values were factorized into a steric component (molecular volume V, mainly accounting for inductive and hydrophobic forces) and a polarity factor (Λ, accounting for ion–dipole and dipole–dipole interactions and hydrogen-bonds) which correlates with other amino acid parameters expressing mainly polar interactions. Using two examples from the literature, we show that multiple linear regression analysis based on steric and polar parameters is able to afford a quantitative interpretation of factors influencing protein conformational stability.
Keywords
Steric effectsPartition coefficientChemistryPolarChemical polarityAmino acidDipoleHydrogen bondChromatographyHydrophobic effectPartition (number theory)Polarity (international relations)StereochemistryComputational chemistryMoleculeOrganic chemistryPhysics
Related Publications
Protein-Protein Interfaces: Architectures and Interactions in Protein-Protein Interfaces and in Protein Cores. Their Similarities and Differences
Protein structures generally consist of favorable folding motifs formed by specific arrangements of secondary structure elements. Similar architectures can be adopted by differe...
Automatic Equipment for Determination of Amino Acids Separation on Columns of Ion Exchange Resins
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAutomatic Equipment for Determination of Amino Acids Separation on Columns of Ion Exchange ResinsD. H. SimmondsCite this: Anal. Chem....
Enumeration of human colonic bacteria producing phenolic and indolic compounds: effects of pH, carbohydrate availability and retention time on dissimilatory aromatic amino acid metabolism
E.A. SMITH AND G.T. MACFARLANE. 1996. Concentrations of phenolic compounds in human gut contents were more than fourfold higher in the distal colon (6.2 mmol kg ‐1 ) compared to...
MolProbity: all-atom contacts and structure validation for proteins and nucleic acids
MolProbity is a general-purpose web server offering quality validation for 3D structures of proteins, nucleic acids and complexes. It provides detailed all-atom contact analysis...
Nucleophilic Degradation of Fenitrothion Insecticide and Performance of Nucleophiles: A Computational Study
Ab initio and density functional theory (DFT) calculations have been performed to understand the destruction chemistry of an important organophosphorus insecticide O,O-dimethyl ...
Publication Info
- Year
- 1992
- Type
- article
- Issue
- 1
- Pages
- 79-84
- Citations
- 86
- Access
- Closed
External Links
Social Impact
Altmetric
PlumX Metrics
Social media, news, blog, policy document mentions
Citation Metrics
86
OpenAlex
Cite This
Nabil El Tayar,
Ruey‐Shiuan Tsai,
Pierre‐Alain Carrupt
et al.
(1992).
Octan-1-ol–water partition coefficients of zwitterionic α-amino acids. Determination by centrifugal partition chromatography and factorization into steric/hydrophobic and polar components.
Journal of the Chemical Society Perkin Transactions 2
(1)
, 79-84.
https://doi.org/10.1039/p29920000079
Identifiers
- DOI
- 10.1039/p29920000079