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R6 hexameric insulin complexed with m-cresol or resorcinol.

Smith GD, Ciszak E, Magrum LA, Pangborn WA, Blessing RH
Acta Crystallogr D Biol Crystallogr 56 1541-8 (2000)
Related entries: 1ev3, 1ev6

Cited: 21 times
EuropePMC logo PMID: 11092919

Abstract

The structures of three R(6) human insulin hexamers have been determined. Crystals of monoclinic m-cresol-insulin, monoclinic resorcinol-insulin and rhombohedral m-cresol-insulin diffracted to 1. 9, 1.9 and 1.78 A, respectively, and have been refined to residuals of 0.195, 0.179 and 0.200, respectively. In all three structures, a phenolic derivative is found to occupy the phenolic binding site, where it forms hydrogen bonds to the carbonyl O atom of CysA6 and the N atom of CysA11. Two additional phenolic derivative binding sites were identified within or between hexamers. The structures of all three hexamers are nearly identical, although a large displacement of the N-terminus of one B chain in both monoclinic structures results from coordination to a sodium ion which is located between symmetry-related hexamers. Other minor differences in structure arise from differences in packing in the monoclinic cell compared with the rhombohedral cell. Based upon the differences in conformation of the GluB13 side chains in T(6), T(3)R(f)(3) and R(6) hexamers, the deprotonation of these side chains appears to be associated with the T-->R conformational transition.

Reviews - 1evr mentioned but not cited (1)

  1. In Quest for Improved Drugs against Diabetes: The Added Value of X-ray Powder Diffraction Methods. Karavassili F, Valmas A, Fili S, Georgiou CD, Margiolaki I. Biomolecules 7 (2017)

Articles - 1evr mentioned but not cited (5)

  1. Crystallographic characterization of two novel crystal forms of human insulin induced by chaotropic agents and a shift in pH. Norrman M, Schluckebier G. BMC Struct. Biol. 7 83 (2007)
  2. Structural signatures of the complex formed between 3-nitro-4-hydroxybenzoate and the Zn(II)-substituted R(6) insulin hexamer. Olsen HB, Leuenberger-Fisher MR, Kadima W, Borchardt D, Kaarsholm NC, Dunn MF. Protein Sci. 12 1902-1913 (2003)
  3. Human insulin polymorphism upon ligand binding and pH variation: the case of 4-ethylresorcinol. Fili S, Valmas A, Norrman M, Schluckebier G, Beckers D, Degen T, Wright J, Fitch A, Gozzo F, Giannopoulou AE, Karavassili F, Margiolaki I. IUCrJ 2 534-544 (2015)
  4. Insulin Hexamer-Caged Gadolinium Ion as MRI Contrast-o-phore. Taylor SK, Tran TH, Liu MZ, Harris PE, Sun Y, Jambawalikar SR, Tong L, Stojanovic MN. Chemistry 24 10646-10652 (2018)
  5. Novel four-disulfide insulin analog with high aggregation stability and potency. Xiong X, Blakely A, Karra P, VandenBerg MA, Ghabash G, Whitby F, Zhang YW, Webber MJ, Holland WL, Hill CP, Chou DH. Chem Sci 11 195-200 (2020)


Articles citing this publication (15)

  1. Minimal functional sites allow a classification of zinc sites in proteins. Andreini C, Bertini I, Cavallaro G. PLoS ONE 6 e26325 (2011)
  2. Contribution of TyrB26 to the Function and Stability of Insulin: STRUCTURE-ACTIVITY RELATIONSHIPS AT A CONSERVED HORMONE-RECEPTOR INTERFACE. Pandyarajan V, Phillips NB, Rege N, Lawrence MC, Whittaker J, Weiss MA. J. Biol. Chem. 291 12978-12990 (2016)
  3. Aromatic anchor at an invariant hormone-receptor interface: function of insulin residue B24 with application to protein design. Pandyarajan V, Smith BJ, Phillips NB, Whittaker L, Cox GP, Wickramasinghe N, Menting JG, Wan ZL, Whittaker J, Ismail-Beigi F, Lawrence MC, Weiss MA. J. Biol. Chem. 289 34709-34727 (2014)
  4. Crystal structure of ultralente--a microcrystalline insulin suspension. Wagner A, Diez J, Schulze-Briese C, Schluckebier G. Proteins 74 1018-1027 (2009)
  5. Structural characterization of insulin NPH formulations. Norrman M, Hubálek F, Schluckebier G. Eur J Pharm Sci 30 414-423 (2007)
  6. Controlled self-assembly of re-engineered insulin by Fe(II). Munch HK, Heide ST, Christensen NJ, Hoeg-Jensen T, Thulstrup PW, Jensen KJ. Chemistry 17 7198-7204 (2011)
  7. Extending Halogen-based Medicinal Chemistry to Proteins: IODO-INSULIN AS A CASE STUDY. El Hage K, Pandyarajan V, Phillips NB, Smith BJ, Menting JG, Whittaker J, Lawrence MC, Meuwly M, Weiss MA. J. Biol. Chem. 291 27023-27041 (2016)
  8. Effect of ethylenediamine on chemical degradation of insulin aspart in pharmaceutical solutions. Poulsen C, Jacobsen D, Palm L. Pharm Res 25 2534-2544 (2008)
  9. 4S-Hydroxylation of Insulin at ProB28 Accelerates Hexamer Dissociation and Delays Fibrillation. Lieblich SA, Fang KY, Cahn JKB, Rawson J, LeBon J, Ku HT, Tirrell DA. J. Am. Chem. Soc. 139 8384-8387 (2017)
  10. Hydrophobic Interaction Between Domain I of Albumin and B Chain of Detemir May Support Myristate-Dependent Detemir-Albumin Binding. Fatima S, Sen P, Sneha P, Priyadoss CG. Appl. Biochem. Biotechnol. 182 82-96 (2017)
  11. Metal induced structural changes observed in hexameric insulin. Sreekanth R, Pattabhi V, Rajan SS. Int. J. Biol. Macromol. 44 29-36 (2009)
  12. 1H[19F] NOE NMR structural signatures of the insulin R6 hexamer: evidence of a capped HisB10 site in aryl- and arylacryloyl-carboxylate complexes. Keidel D, Bonaccio M, Ghaderi N, Niks D, Borchardt D, Dunn MF. Chembiochem 10 450-453 (2009)
  13. Formation of Protamine and Zn-Insulin Assembly: Exploring Biophysical Consequences. Aggarwal S, Tanwar N, Singh A, Munde M. ACS Omega 7 41044-41057 (2022)
  14. Incorporation of Aliphatic Proline Residues into Recombinantly Produced Insulin. Breunig SL, Quijano JC, Donohue C, Henrickson A, Demeler B, Ku HT, Tirrell DA. ACS Chem Biol 18 2574-2581 (2023)
  15. Unraveling the Impact of pH on the Crystallization of Pharmaceutical Proteins: A Case Study of Human Insulin. Link FJ, Heng JYY. Cryst Growth Des 22 3024-3033 (2022)


Related citations provided by authors (2)

  1. Structure of a Rhombohedral R6 Insuliin/Phenol Complex. Smith GD, Dodson GG Proteins 14 401-408 (1992)
  2. Phenol stabilizes more helix in a new symmetrical zinc insulin hexamer.. Derewenda U, Derewenda Z, Dodson EJ, Dodson GG, Reynolds CD, Smith GD, Sparks C, Swenson D Nature 338 594-6 (1989)

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