title: Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids.
abstract: Hydrophobicity has proven to be an extremely useful parameter in small molecule drug discovery programmes given that it can be used as a predictive tool to enable rational design. For larger molecules, including peptoids, where folding is possible, the situation is more complicated and the average hydrophobicity (as determined by RP-HPLC retention time) may not always provide an effective predictive tool for rational design. Herein, we report the first ever application of partitioning experiments to determine the log D values for a series of peptoids. By comparing log D and average hydrophobicities we highlight the potential advantage of employing the former as a predictive tool in the rational design of biologically active peptoids.
authors.affiliation: Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United Kingdom.
authors.forename: H L
authors.initials: HL
authors.lastname: Bolt
authors.affiliation: Department of Physics, Durham University, South Road, Durham, DH1 3LE, United Kingdom.
authors.forename: C E J
authors.initials: CEJ
authors.lastname: Williams
authors.affiliation: Department of Physics, Durham University, South Road, Durham, DH1 3LE, United Kingdom.
authors.forename: R V
authors.initials: RV
authors.lastname: Brooks
authors.affiliation: Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, California.
authors.forename: R N
authors.initials: RN
authors.lastname: Zuckermann
authors.affiliation: Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United Kingdom.
authors.forename: S L
authors.initials: SL
authors.lastname: Cobb
authors.affiliation: Department of Physics, Durham University, South Road, Durham, DH1 3LE, United Kingdom.
authors.forename: E H C
authors.initials: EHC
authors.lastname: Bromley
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D057927:Hydrophobic and Hydrophilic Interactions; D019151:Peptide Library; D034444:Peptoids / Q000737:chemistry*
chemical_list: D019151:Peptide Library; D034444:Peptoids