Hydrogen bonding. 47. Characterization of the ethylene glycol–heptane partition system: Hydrogen bond acidity and basicity of peptides
- 1 February 1999
- journal article
- Published by American Geophysical Union (AGU) in Journal of Pharmaceutical Sciences
- Vol. 88 (2), 241-247
- https://doi.org/10.1021/js980242l
Abstract
Twelve measured ethylene glycol-heptane partition coefficients, Peh, have been combined with 20 measured literature values and 44 indirectly determined values to give a set of 76 values. Excluding one value for benzamide, the log Peh values are correlated through our general solvation equation, log Peh = 0.336 - 0.075R2 - 1. 201pi2H - 3.786 Sigmaalpha2H - 2.201 Sigmabeta2H + 2.085Vx with r2 = 0.966, sd = 0.28, and F = 386. The solute descriptor R2 is the excess molar refraction, pi2H is the dipolarity/polarizability, Sigmaalpha2H and Sigmabeta2H are the overall hydrogen bond acidity and basicity, and Vx is the McGowan volume. The log Peh equation has then been used to obtain descriptors for eleven peptides, all of which are end-protected. It is shown that for these end-protected peptides, hydrogen bond basicity makes a greater contribution to log Peh than does hydrogen bond acidity.Keywords
This publication has 29 references indexed in Scilit:
- A Non‐aqueous Partitioning System for Predicting the Oral Absorption Potential of PeptidesQuantitative Structure-Activity Relationships, 1994
- Hydrogen Bonding Potential as a Determinant of the in Vitro and in Situ Blood–Brain Barrier Permeability of PeptidesPharmaceutical Research, 1994
- Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processesChemical Society Reviews, 1993
- The relationship between peptide structure and transport across epithelial cell monolayersJournal of Controlled Release, 1992
- Desolvation Energy: A Major Determinant of Absorption, But Not Clearance, of Peptides in RatsPharmaceutical Research, 1991
- The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatographyChromatographia, 1987
- Solubility of hydrogen in 10 organic solvents at 298.15, 323.15, and 373.15 KJournal of Chemical & Engineering Data, 1985
- The Solubility of Nitrogen and Air in LiquidsJournal of Physical and Chemical Reference Data, 1984
- Thermodynamic functions of the solubilities of gases in liquids at 25.deg.Chemical Reviews, 1973
- The Solubility of Helium, Neon, Argon and Krypton in Some Hydrocarbon SolventsThe Journal of Physical Chemistry, 1957