Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids

Bolt, H. L.; Williams, C. E. J.; Brooks, R. V.; Zuckermann, R. N.; Cobb, S. L.; Bromley, E. H. C.

doi:10.1002/bip.23014

Title: Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids

Journal Article · Mon Jan 09 00:00:00 EST 2017 · Biopolymers

DOI:https://doi.org/10.1002/bip.23014· OSTI ID:1366313

Bolt, H. L. ^[1]; Williams, C. E. J. ^[2]; Brooks, R. V. ^[2]; Zuckermann, R. N. ^[3]; Cobb, S. L. ^[1]; Bromley, E. H. C. ^[2]

Department of Chemistry, Durham University, South Road Durham DH1 3LE United Kingdom
Department of Physics, Durham University, South Road Durham DH1 3LE United Kingdom
Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley California

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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1366313

Alternate ID(s):: OSTI ID: 1366314; OSTI ID: 1409436

Journal Information:: Biopolymers, Journal Name: Biopolymers Vol. 108 Journal Issue: 4; ISSN 0006-3525

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 12 works

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Title: Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids

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