1hpn Citations

N.m.r. and molecular-modelling studies of the solution conformation of heparin.

Biochem. J. 293 ( Pt 3) 849-58 (1993)
Cited: 231 times
EuropePMC logo PMID: 8352752


The solution conformations of heparin and de-N-sulphated, re-N-acetylated heparin have been determined by a combination of n.m.r. spectroscopic and molecular-modelling techniques. The 1H- and 13C-n.m.r. spectra of these polysaccharides have been assigned. Observed 1H-1H nuclear Overhauser enhancements (n.O.e.s) have been simulated using the program NOEMOL [Forster, Jones and Mulloy (1989) J. Mol. Graph. 7, 196-201] for molecular models derived from conformational-energy calculations; correlation times for the simulations were chosen to fit experimentally determined 13C spin-lattice relaxation times. In order to achieve good agreement between calculated and observed 1H-1H n.O.e.s it was necessary to assume that the reorientational motion of the polysaccharide molecules was not isotropic, but was that of a symmetric top. The resulting model of heparin in solution is similar to that determined in the fibrous state by X-ray-diffraction techniques [Nieduszynski, Gardner and Atkins (1977) Am. Chem. Soc. Symp. Ser. 48, 73-80].

Reviews - 1hpn mentioned but not cited (7)

  1. Synthetic Oligosaccharide Libraries and Microarray Technology: A Powerful Combination for the Success of Current Glycosaminoglycan Interactomics. Pomin VH, Wang X. ChemMedChem 13 648-661 (2018)
  2. The Sea as a Rich Source of Structurally Unique Glycosaminoglycans and Mimetics. Vasconcelos AA, Pomin VH. Microorganisms 5 (2017)
  3. Extracellular regulation of type IIa receptor protein tyrosine phosphatases: mechanistic insights from structural analyses. Coles CH, Jones EY, Aricescu AR. Semin. Cell Dev. Biol. 37 98-107 (2015)
  4. Heparan sulfate-protein binding specificity. Nugent MA, Zaia J, Spencer JL. Biochemistry Mosc. 78 726-735 (2013)
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  7. Specific sides to multifaceted glycosaminoglycans are observed in embryonic development. Kramer KL. Semin. Cell Dev. Biol. 21 631-637 (2010)

Articles - 1hpn mentioned but not cited (53)

  1. Identification of a heparin-binding motif on adeno-associated virus type 2 capsids. Kern A, Schmidt K, Leder C, Müller OJ, Wobus CE, Bettinger K, Von der Lieth CW, King JA, Kleinschmidt JA. J. Virol. 77 11072-11081 (2003)
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  3. Structural diversity of heparan sulfate binding domains in chemokines. Lortat-Jacob H, Grosdidier A, Imberty A. Proc. Natl. Acad. Sci. U.S.A. 99 1229-1234 (2002)
  4. Characterization of the structural features and interactions of sclerostin: molecular insight into a key regulator of Wnt-mediated bone formation. Veverka V, Henry AJ, Slocombe PM, Ventom A, Mulloy B, Muskett FW, Muzylak M, Greenslade K, Moore A, Zhang L, Gong J, Qian X, Paszty C, Taylor RJ, Robinson MK, Carr MD. J. Biol. Chem. 284 10890-10900 (2009)
  5. Structural basis for complement factor H linked age-related macular degeneration. Prosser BE, Johnson S, Roversi P, Herbert AP, Blaum BS, Tyrrell J, Jowitt TA, Clark SJ, Clark SJ, Tarelli E, Uhrín D, Barlow PN, Sim RB, Day AJ, Lea SM. J. Exp. Med. 204 2277-2283 (2007)
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  7. Binding and clustering of glycosaminoglycans: a common property of mono- and multivalent cell-penetrating compounds. Ziegler A, Seelig J. Biophys. J. 94 2142-2149 (2008)
  8. The novel CXCL12gamma isoform encodes an unstructured cationic domain which regulates bioactivity and interaction with both glycosaminoglycans and CXCR4. Laguri C, Sadir R, Rueda P, Baleux F, Gans P, Arenzana-Seisdedos F, Lortat-Jacob H. PLoS ONE 2 e1110 (2007)
  9. Characterization of the interaction of interleukin-8 with hyaluronan, chondroitin sulfate, dermatan sulfate and their sulfated derivatives by spectroscopy and molecular modeling. Pichert A, Samsonov SA, Theisgen S, Thomas L, Baumann L, Schiller J, Beck-Sickinger AG, Huster D, Pisabarro MT. Glycobiology 22 134-145 (2012)
  10. The layered fold of the TSR domain of P. falciparum TRAP contains a heparin binding site. Tossavainen H, Pihlajamaa T, Huttunen TK, Raulo E, Rauvala H, Permi P, Kilpeläinen I. Protein Sci. 15 1760-1768 (2006)
  11. Characterization of heparin-binding site of tissue transglutaminase: its importance in cell surface targeting, matrix deposition, and cell signaling. Wang Z, Collighan RJ, Pytel K, Rathbone DL, Li X, Griffin M. J. Biol. Chem. 287 13063-13083 (2012)
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  13. Mechanism of amylin fibrillization enhancement by heparin. Jha S, Patil SM, Gibson J, Nelson CE, Alder NN, Alexandrescu AT. J. Biol. Chem. 286 22894-22904 (2011)
  14. Two distinct sites in sonic Hedgehog combine for heparan sulfate interactions and cell signaling functions. Chang SC, Mulloy B, Magee AI, Couchman JR. J. Biol. Chem. 286 44391-44402 (2011)
  15. Characterization of the chemokine CXCL11-heparin interaction suggests two different affinities for glycosaminoglycans. Severin IC, Gaudry JP, Johnson Z, Kungl A, Jansma A, Gesslbauer B, Mulloy B, Power C, Proudfoot AE, Handel T. J. Biol. Chem. 285 17713-17724 (2010)
  16. Solution NMR characterization of chemokine CXCL8/IL-8 monomer and dimer binding to glycosaminoglycans: structural plasticity mediates differential binding interactions. Joseph PR, Mosier PD, Desai UR, Rajarathnam K. Biochem. J. 472 121-133 (2015)
  17. Structure of a Plasmodium falciparum PfEMP1 rosetting domain reveals a role for the N-terminal segment in heparin-mediated rosette inhibition. Juillerat A, Lewit-Bentley A, Guillotte M, Gangnard S, Hessel A, Baron B, Vigan-Womas I, England P, Mercereau-Puijalon O, Bentley GA. Proc. Natl. Acad. Sci. U.S.A. 108 5243-5248 (2011)
  18. Transglutaminase-2 interaction with heparin: identification of a heparin binding site that regulates cell adhesion to fibronectin-transglutaminase-2 matrix. Lortat-Jacob H, Burhan I, Scarpellini A, Thomas A, Imberty A, Vivès RR, Johnson T, Gutierrez A, Verderio EA. J. Biol. Chem. 287 18005-18017 (2012)
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  20. Molecular basis of glycosaminoglycan heparin binding to the chemokine CXCL1 dimer. Poluri KM, Joseph PR, Sawant KV, Rajarathnam K. J. Biol. Chem. 288 25143-25153 (2013)
  21. Docking glycosaminoglycans to proteins: analysis of solvent inclusion. Samsonov SA, Teyra J, Pisabarro MT. J. Comput. Aided Mol. Des. 25 477-489 (2011)
  22. CXCL1/MGSA Is a Novel Glycosaminoglycan (GAG)-binding Chemokine: STRUCTURAL EVIDENCE FOR TWO DISTINCT NON-OVERLAPPING BINDING DOMAINS. Sepuru KM, Rajarathnam K. J. Biol. Chem. 291 4247-4255 (2016)
  23. Influence of heparin mimetics on assembly of the FGF.FGFR4 signaling complex. Saxena K, Schieborr U, Anderka O, Duchardt-Ferner E, Elshorst B, Gande SL, Janzon J, Kudlinzki D, Sreeramulu S, Dreyer MK, Wendt KU, Herbert C, Duchaussoy P, Bianciotto M, Driguez PA, Lassalle G, Savi P, Mohammadi M, Bono F, Schwalbe H. J. Biol. Chem. 285 26628-26640 (2010)
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  25. Heparin/heparan sulfate 6-O-sulfatase from Flavobacterium heparinum: integrated structural and biochemical investigation of enzyme active site and substrate specificity. Myette JR, Soundararajan V, Shriver Z, Raman R, Sasisekharan R. J. Biol. Chem. 284 35177-35188 (2009)
  26. Preclinical Validation of the Heparin-Reactive Peptide p5+14 as a Molecular Imaging Agent for Visceral Amyloidosis. Wall JS, Martin EB, Richey T, Stuckey AC, Macy S, Wooliver C, Williams A, Foster JS, McWilliams-Koeppen P, Uberbacher E, Cheng X, Kennel SJ. Molecules 20 7657-7682 (2015)
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  28. Molecular Basis of Chemokine CXCL5-Glycosaminoglycan Interactions. Sepuru KM, Nagarajan B, Desai UR, Rajarathnam K. J. Biol. Chem. 291 20539-20550 (2016)
  29. Molecular interaction studies of HIV-1 matrix protein p17 and heparin: identification of the heparin-binding motif of p17 as a target for the development of multitarget antagonists. Bugatti A, Giagulli C, Urbinati C, Caccuri F, Chiodelli P, Oreste P, Fiorentini S, Orro A, Milanesi L, D'Ursi P, Caruso A, Rusnati M. J. Biol. Chem. 288 1150-1161 (2013)
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  32. Mechanism of heparin acceleration of tissue inhibitor of metalloproteases-1 (TIMP-1) degradation by the human neutrophil elastase. Nunes GL, Simões A, Dyszy FH, Shida CS, Juliano MA, Juliano L, Gesteira TF, Nader HB, Murphy G, Chaffotte AF, Goldberg ME, Tersariol IL, Almeida PC. PLoS ONE 6 e21525 (2011)
  33. Platelet-Derived Chemokine CXCL7 Dimer Preferentially Exists in the Glycosaminoglycan-Bound Form: Implications for Neutrophil-Platelet Crosstalk. Brown AJ, Sepuru KM, Sawant KV, Rajarathnam K. Front Immunol 8 1248 (2017)
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  36. Structural Basis of Native CXCL7 Monomer Binding to CXCR2 Receptor N-Domain and Glycosaminoglycan Heparin. Brown AJ, Sepuru KM, Rajarathnam K. Int J Mol Sci 18 (2017)
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  40. Identification of the Glycosaminoglycan Binding Site of Interleukin-10 by NMR Spectroscopy. Künze G, Köhling S, Vogel A, Rademann J, Huster D. J. Biol. Chem. 291 3100-3113 (2016)
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  42. Inhibition of Mammalian Glycoprotein YKL-40: IDENTIFICATION OF THE PHYSIOLOGICAL LIGAND. Kognole AA, Payne CM. J. Biol. Chem. 292 2624-2636 (2017)
  43. A haplotype in CFH family genes confers high risk of rare glomerular nephropathies. Ding Y, Zhao W, Zhang T, Qiang H, Lu J, Su X, Wen S, Xu F, Zhang M, Zhang H, Zeng C, Liu Z, Chen H. Sci Rep 7 6004 (2017)
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  45. Endocytotic routes of cobra cardiotoxins depend on spatial distribution of positively charged and hydrophobic domains to target distinct types of sulfated glycoconjugates on cell surface. Lee SC, Lin CC, Wang CH, Wu PL, Huang HW, Chang CI, Wu WG. J. Biol. Chem. 289 20170-20181 (2014)
  46. Heparan Sulfate Organizes Neuronal Synapses through Neurexin Partnerships. Zhang P, Lu H, Peixoto RT, Pines MK, Ge Y, Oku S, Siddiqui TJ, Xie Y, Wu W, Archer-Hartmann S, Yoshida K, Tanaka KF, Aricescu AR, Azadi P, Gordon MD, Sabatini BL, Wong ROL, Craig AM. Cell 174 1450-1464.e23 (2018)
  47. Facile saccharide-free mimetics that recapitulate key features of glycosaminoglycan sulfation patterns. Lim TC, Cai S, Huber RG, Bond PJ, Siew Chia PX, Khou SL, Gao S, Lee SS, Lee SG. Chem Sci 9 7940-7947 (2018)
  48. Design and synthesis of biphenyl and biphenyl ether inhibitors of sulfatases. Reuillon T, Alhasan SF, Beale GS, Bertoli A, Brennan A, Cano C, Reeves HL, Newell DR, Golding BT, Miller DC, Griffin RJ. Chem Sci 7 2821-2826 (2016)
  49. Glycosaminoglycan monosaccharide blocks analysis by quantum mechanics, molecular dynamics, and nuclear magnetic resonance. Samsonov SA, Theisgen S, Riemer T, Huster D, Pisabarro MT. Biomed Res Int 2014 808071 (2014)
  50. Structural basis, stoichiometry, and thermodynamics of binding of the chemokines KC and MIP2 to the glycosaminoglycan heparin. Sepuru KM, Nagarajan B, Desai UR, Rajarathnam K. J. Biol. Chem. 293 17817-17828 (2018)
  51. The localisation of the heparin binding sites of human and murine interleukin-12 within the carboxyterminal domain of the P40 subunit. Garnier P, Mummery R, Forster MJ, Mulloy B, Gibbs RV, Rider CC. Cytokine 110 159-168 (2018)
  52. TriplatinNC and Biomolecules: Building Models Based on Non-covalent Interactions. Rosa NMP, Ferreira FHDC, Farrell NP, Costa LAS. Front Chem 7 307 (2019)
  53. Unraveling Heparan Sulfate Proteoglycan Binding Motif for Cancer Cell Selectivity. Brunetti J, Riolo G, Depau L, Mandarini E, Bernini A, Karousou E, Passi A, Pini A, Bracci L, Falciani C. Front Oncol 9 843 (2019)

Reviews citing this publication (30)

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Articles citing this publication (141)

  1. Crystal structure of a ternary FGF-FGFR-heparin complex reveals a dual role for heparin in FGFR binding and dimerization. Schlessinger J, Plotnikov AN, Ibrahimi OA, Eliseenkova AV, Yeh BK, Yayon A, Linhardt RJ, Mohammadi M. Mol. Cell 6 743-750 (2000)
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