Literature DB >> 24186046

Lipophilicity of amino acids.

H van de Waterbeemd1, H Karajiannis, N El Tayar.   

Abstract

The lipophilicity (or hydrophobicity) of amino acids is an important property relevant for protein folding and therefore of great interest in protein engineering. For peptides or peptidomimetics of potential therapeutic interest, lipophilicity is related to absorption and distribution, and thus indirectly relates to their bioactivity. A rationalization of peptide lipophilicity requires basic knowledge of the lipophilicity of the constituting amino acids. In the present contribution we will review methods to measure or calculate the lipophilicities of amino acids, including unusual amino acids, and we will make a comparison between various lipophilicity scales.

Year:  1994        PMID: 24186046     DOI: 10.1007/BF00814156

Source DB:  PubMed          Journal:  Amino Acids        ISSN: 0939-4451            Impact factor:   3.520


  31 in total

1.  Development of hydrophobicity parameters to analyze proteins which bear post- or cotranslational modifications.

Authors:  S D Black; D R Mould
Journal:  Anal Biochem       Date:  1991-02-15       Impact factor: 3.365

2.  Minimum analogue peptide sets (MAPS) for quantitative structure-activity relationships.

Authors:  S Hellberg; L Eriksson; J Jonsson; F Lindgren; M Sjöström; B Skagerberg; S Wold; P Andrews
Journal:  Int J Pept Protein Res       Date:  1991-05

3.  New hydrophilicity scale derived from high-performance liquid chromatography peptide retention data: correlation of predicted surface residues with antigenicity and X-ray-derived accessible sites.

Authors:  J M Parker; D Guo; R S Hodges
Journal:  Biochemistry       Date:  1986-09-23       Impact factor: 3.162

4.  Hydrophilicity of polar amino acid side-chains is markedly reduced by flanking peptide bonds.

Authors:  M A Roseman
Journal:  J Mol Biol       Date:  1988-04-05       Impact factor: 5.469

5.  Amino acid preferences for specific locations at the ends of alpha helices.

Authors:  J S Richardson; D C Richardson
Journal:  Science       Date:  1988-06-17       Impact factor: 47.728

6.  Surface tension of amino acid solutions: a hydrophobicity scale of the amino acid residues.

Authors:  H B Bull; K Breese
Journal:  Arch Biochem Biophys       Date:  1974-04-02       Impact factor: 4.013

Review 7.  Determination of hydrophobic parameters by reversed-phase liquid chromatography: theory, experimental techniques, and application in studies on quantitative structure-activity relationships.

Authors:  T Braumann
Journal:  J Chromatogr       Date:  1986-11-14

8.  Peptide quantitative structure-activity relationships, a multivariate approach.

Authors:  S Hellberg; M Sjöström; B Skagerberg; S Wold
Journal:  J Med Chem       Date:  1987-07       Impact factor: 7.446

9.  Hydrophobicity of amino acid residues in globular proteins.

Authors:  G D Rose; A R Geselowitz; G J Lesser; R H Lee; M H Zehfus
Journal:  Science       Date:  1985-08-30       Impact factor: 47.728

10.  A simple method for displaying the hydropathic character of a protein.

Authors:  J Kyte; R F Doolittle
Journal:  J Mol Biol       Date:  1982-05-05       Impact factor: 5.469

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  5 in total

1.  Structure-lipophilicity relationships of peptides and peptidomimetics.

Authors:  N El Tayar; H Karajiannis; H van de Waterbeemd
Journal:  Amino Acids       Date:  1995-06       Impact factor: 3.520

2.  Characterizing hydrophobicity of amino acid side chains in a protein environment via measuring contact angle of a water nanodroplet on planar peptide network.

Authors:  Chongqin Zhu; Yurui Gao; Hui Li; Sheng Meng; Lei Li; Joseph S Francisco; Xiao Cheng Zeng
Journal:  Proc Natl Acad Sci U S A       Date:  2016-11-01       Impact factor: 11.205

3.  Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid.

Authors:  Francisco J Sayago; M Isabel Calaza; Ana I Jiménez; Carlos Cativiela
Journal:  Tetrahedron       Date:  2008-01-01       Impact factor: 2.457

4.  Bioinformatics analysis of adhesin-binding potential and ADME/Tox profile of anti-Helicobacter pylori peptides derived from wheat germ proteins.

Authors:  Chi Dang; Ogadimma Okagu; Xiaohong Sun; Chibuike C Udenigwe
Journal:  Heliyon       Date:  2022-06-03

5.  Cyclotide structure-activity relationships: qualitative and quantitative approaches linking cytotoxic and anthelmintic activity to the clustering of physicochemical forces.

Authors:  Sungkyu Park; Adam A Strömstedt; Ulf Göransson
Journal:  PLoS One       Date:  2014-03-28       Impact factor: 3.240

  5 in total

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