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Two modes of fatty acid binding to bovine β-lactoglobulin--crystallographic and spectroscopic studies.

Loch J, Polit A, Górecki A, Bonarek P, Kurpiewska K, Dziedzicka-Wasylewska M, Lewiński K
J Mol Recognit 24 341-9 (2011)
Related entries: 3nq3, 3nq9

Cited: 46 times
EuropePMC logo PMID: 21360616

Abstract

Lactoglobulin is a natural protein present in bovine milk and common component of human diet, known for binding with high affinity wide range of hydrophobic compounds, among them fatty acids 12-20 carbon atoms long. Shorter fatty acids were reported as not binding to β-lactoglobulin. We used X-ray crystallography and fluorescence spectroscopy to show that lactoglobulin binds also 8- and 10-carbon caprylic and capric acids, however with lower affinity. The determined apparent association constant for lactoglobulin complex with caprylic acid is 10.8 ± 1.7 × 10(3) M(-1), while for capric acid is 6.0 ± 0.5 × 10(3) M(-1). In crystal structures determined with resolution 1.9 Å the caprylic acid is bound in upper part of central calyx near polar residues located at CD loop, while the capric acid is buried deeper in the calyx bottom and does not interact with polar residues at CD loop. In both structures, water molecule hydrogen-bonded to carboxyl group of fatty acid is observed. Different location of ligands in the binding site indicates that competition between polar and hydrophobic interactions is an important factor determining position of the ligand in β-barrel.

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Reviews citing this publication (1)

  1. Structural similarities of human and mammalian lipocalins, and their function in innate immunity and allergy. Jensen-Jarolim E, Pacios LF, Bianchini R, Hofstetter G, Roth-Walter F. Allergy 71 286-294 (2016)

Articles citing this publication (27)

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  2. Hybrid Steered Molecular Dynamics Approach to Computing Absolute Binding Free Energy of Ligand-Protein Complexes: A Brute Force Approach That Is Fast and Accurate. Chen LY. J Chem Theory Comput 11 1928-1938 (2015)
  3. Binding of 18-carbon unsaturated fatty acids to bovine β-lactoglobulin--structural and thermodynamic studies. Loch JI, Bonarek P, Polit A, Riès D, Dziedzicka-Wasylewska M, Lewiński K. Int J Biol Macromol 57 226-231 (2013)
  4. Precise, fast and flexible determination of protein interactions by affinity capillary electrophoresis. Part 2: cations. Redweik S, Cianciulli C, Hara M, Xu Y, Wätzig H. Electrophoresis 34 1812-1819 (2013)
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  6. Binding free energy calculations between bovine β-lactoglobulin and four fatty acids using the MMGBSA method. Bello M. Biopolymers 101 1010-1018 (2014)
  7. The differences in binding 12-carbon aliphatic ligands by bovine β-lactoglobulin isoform A and B studied by isothermal titration calorimetry and X-ray crystallography. Loch JI, Bonarek P, Polit A, Swiątek Ś, Dziedzicka-Wasylewska M, Lewiński K. J Mol Recognit 26 357-367 (2013)
  8. Interaction of Quillaja bark saponins with food-relevant proteins. Kezwon A, Wojciechowski K. Adv Colloid Interface Sci 209 185-195 (2014)
  9. Molecular simulations of β-lactoglobulin complexed with fatty acids reveal the structural basis of ligand affinity to internal and possible external binding sites. Evoli S, Guzzi R, Rizzuti B. Proteins 82 2609-2619 (2014)
  10. Electrostatic interactions play an essential role in the binding of oleic acid with α-lactalbumin in the HAMLET-like complex: a study using charge-specific chemical modifications. Xie Y, Min S, Harte NP, Kirk H, O'Brien JE, Voorheis HP, Svanborg C, Hun Mok K. Proteins 81 1-17 (2013)
  11. Influence of Alkylammonium Acetate Buffers on Protein-Ligand Noncovalent Interactions Using Native Mass Spectrometry. Zhuang X, Gavriilidou AFM, Zenobi R. J Am Soc Mass Spectrom 28 341-346 (2017)
  12. β-lactoglobulin's conformational requirements for ligand binding at the calyx and the dimer interphase: a flexible docking study. Domínguez-Ramírez L, Del Moral-Ramírez E, Cortes-Hernández P, García-Garibay M, Jiménez-Guzmán J. PLoS One 8 e79530 (2013)
  13. Factors affecting the interactions between beta-lactoglobulin and fatty acids as revealed in molecular dynamics simulations. Yi C, Wambo TO. Phys Chem Chem Phys 17 23074-23080 (2015)
  14. Adsorption of Milk Proteins (β-Casein and β-Lactoglobulin) and BSA onto Hydrophobic Surfaces. Pérez-Fuentes L, Drummond C, Faraudo J, Bastos-González D. Materials (Basel) 10 E893 (2017)
  15. Alginate Trisaccharide Binding Sites on the Surface of β-Lactoglobulin Identified by NMR Spectroscopy: Implications for Molecular Network Formation. Stender EGP, Birch J, Kjeldsen C, Nielsen LD, Duus JØ, Kragelund BB, Svensson B. ACS Omega 4 6165-6174 (2019)
  16. Artificial metalloenzymes derived from bovine β-lactoglobulin for the asymmetric transfer hydrogenation of an aryl ketone--synthesis, characterization and catalytic activity. Chevalley A, Cherrier MV, Fontecilla-Camps JC, Ghasemi M, Salmain M. Dalton Trans 43 5482-5489 (2014)
  17. Binding Sites for Oligosaccharide Repeats from Lactic Acid Bacteria Exopolysaccharides on Bovine β-Lactoglobulin Identified by NMR Spectroscopy. Birch J, Khan S, Madsen M, Kjeldsen C, Møller MS, Stender EGP, Peters GHJ, Duus JØ, Kragelund BB, Svensson B. ACS Omega 6 9039-9052 (2021)
  18. Highly Collapsed Conformation of the Initial Folding Intermediates of β-Lactoglobulin with Non-Native α-Helix. Konuma T, Sakurai K, Yagi M, Goto Y, Fujisawa T, Takahashi S. J Mol Biol 427 3158-3165 (2015)
  19. Structure of two crystal forms of sheep β-lactoglobulin with EF-loop in closed conformation. Loch JI, Molenda M, Kopeć M, Swiątek S, Lewiński K. Biopolymers 101 886-894 (2014)
  20. The Interaction of Bovine β-Lactoglobulin with Caffeic Acid: From Binding Mechanisms to Functional Complexes. Stănciuc N, Râpeanu G, Bahrim GE, Aprodu I. Biomolecules 10 E1096 (2020)
  21. β-Lactoglobulin interactions with local anaesthetic drugs – Crystallographic and calorimetric studies. Loch JI, Bonarek P, Polit A, Jabłoński M, Czub M, Ye X, Lewiński K. Int J Biol Macromol 80 87-94 (2015)
  22. Antigenicity of β-lactoglobulin reduced by combining with oleic acid during dynamic high-pressure microfluidization: Multi-spectroscopy and molecule dynamics simulation analysis. Zhong J, Fu S, Yu H, Zhou L, Liu W, Liu C, Prakash S. J Dairy Sci 102 145-154 (2019)
  23. Binding study of novel anti-diabetic pyrimidine fused heterocycles to β-lactoglobulin as a carrier protein. Mehraban MH, Yousefi R, Taheri-Kafrani A, Panahi F, Khalafi-Nezhad A. Colloids Surf B Biointerfaces 112 374-379 (2013)
  24. Effects of polymerized whey protein on goaty flavor and texture properties of fermented goat milk in comparison with β-cyclodextrin. Wang C, Wang C, Gao F, Xu Y, Guo M. J Dairy Res 85 465-471 (2018)
  25. β-Lactoglobulin as a Nanotransporter for Glabridin: Exploring the Binding Properties and Bioactivity Influences. Wei Y, Vriesekoop F, Yuan Q, Liang H. ACS Omega 3 12246-12252 (2018)
  26. New ligand-binding sites identified in the crystal structures of β-lactoglobulin complexes with desipramine. Loch JI, Barciszewski J, Śliwiak J, Bonarek P, Wróbel P, Pokrywka K, Shabalin IG, Minor W, Jaskolski M, Lewiński K. IUCrJ 9 386-398 (2022)
  27. Understanding the potency of fatty acids with the amino acid side chains of bovine β lactoglobulin-A quantum chemical approach. Palanisamy D, Pandiyan BV, Duraisamy T, Kolandaivel P. J Mol Graph Model 74 105-116 (2017)


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