N-PEGylation of a reverse turn is stabilizing in multiple sequence contexts, unlike N-GlcNAcylation

ACS Chemical Biology

Volumn 6, Issue 11, 2011, Pages 1188-1192

  Price, Joshua L ^a   Powers, Evan T ^a   Kelly, Jeffery W ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCAN; MACROGOL;

ARTICLE; GLYCOSYLATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN DENATURATION; PROTEIN FOLDING;

ACETYLGLUCOSAMINE; GLYCOSYLATION; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDYLPROLYL ISOMERASE; POLYETHYLENE GLYCOLS; THERMODYNAMICS;

EID: 81555208976     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb200277u     Document Type: Article

References (30)

1. Abuchowski, A., Vanes, T., Palczuk, N. C., and Davis, F. F. (1977) Alteration of immunological properties of bovine serum-albumin by covalent attachment of polyethylene-glycol J. Biol. Chem. 252, 3578-3581 (Pubitemid 8116087)
2. Frokjaer, S. and Otzen, D. E. (2005) Protein drug stability: A formulation challenge Nat. Rev. Drug Discovery 4, 298-306 (Pubitemid 41130943)
3. Jevsevar, S., Kunstelj, M., and Porekar, V. G. (2010) PEGylation of therapeutic proteins Biotechnol. J. 5, 113-128
4. Kinstler, O. B., Brems, D. N., Lauren, S. L., Paige, A. G., Hamburger, J. B., and Treuheit, M. J. (1996) Characterization and stability of N-terminally PEGylated rhG-CSF Pharm. Res. 13, 996-1002 (Pubitemid 26258997)
5. Dhalluin, C., Ross, A., Leuthold, L. A., Foser, S., Gsell, B., Muller, F., and Senn, H. (2005) Structural and biophysical characterization of the 40 kDa PEG-interferon-alpha(2a) and its individual positional isomers Bioconjugate Chem. 16, 504-517 (Pubitemid 40696041)
6. Rodriguez-Martinez, J. A., Sola, R. J., Castillo, B., Cintron-Colon, H. R., Rivera-Rivera, I., Barletta, G., and Griebenow, K. (2008) Stabilization of alpha-chymotrypsin upon PEGylation correlates with reduced structural dynamics Biotechnol. Bioeng. 101, 1142-1149
7. Chiu, K., Agoubi, L. L., Lee, I., Limpar, M. T., Lowe, J. W., and Goh, S. L. (2010) Effects of polymer molecular weight on the size, activity, and stability of PEG-functionalized trypsin Biomacromolecules 11, 3688-3692
8. Yang, C., Lu, D. N., and Liu, Z. (2011) How PEGylation enhances the stability and potency of insulin: A molecular dynamics simulation Biochemistry 50, 2585-2593
9. So, T., Ueda, T., Abe, Y., Nakamata, T., and Imoto, T. (1996) Situation of monomethoxypolyethylene glycol covalently attached to lysozyme J. Biochem. 119, 1086-1093 (Pubitemid 26202621)
10. Gokarn, Y. R. (2003) Hydrodynamic behavior and thermal stability of a PEGylated protein: Studies with hen egg lysozyme, Ph.D. Dissertation, University of New Hampshire.
11. Callahan, W. J., Narhi, L. O., Kosky, A. A., and Treuheit, M. J. (2001) Sodium chloride enhances the storage and conformational stability of BDNF and PEG-BDNF Pharm. Res. 18, 261-266 (Pubitemid 32595811)
12. Popp, M. W., Dougan, S. K., Chuang, T. Y., Spooner, E., and Ploegh, H. L. (2011) Sortase-catalyzed transformations that improve the properties of cytokines Proc. Natl. Acad. Sci. U.S.A. 108, 3169-3174
13. Plesner, B., Westh, P., and Nielsen, A. D. (2011) Biophysical characterisation of GlycoPEGylated recombinant human factor VIIa Int. J. Pharm. 406, 62-68
14. Walsh, G. and Jefferis, R. (2006) Post-translational modifications in the context of therapeutic proteins Nat. Biotechnol. 24, 1241-1252 (Pubitemid 44564769)
15. Sola, R. J. and Griebenow, K. (2010) Glycosylation of therapeutic proteins: an effective strategy to optimize efficacy Biodrugs 24, 9-21
16. Kornfeld, R. and Kornfeld, S. (1985) Assembly of asparagine-linked oligosaccharides Annu. Rev. Biochem. 54, 631-664 (Pubitemid 15073660)
17. Wormald, M. R., Wooten, E. W., Bazzo, R., Edge, C. J., Feinstein, A., Rademacher, T. W., and Dwek, R. A. (1991) The conformational effects of N-glycosylation on the tailpiece from serum IgM Eur. J. Biochem. 198, 131-139
18. Imperiali, B. and Rickert, K. W. (1995) Conformational implications of asparagine-linked glycosylation Proc. Natl. Acad. Sci. U.S.A. 92, 97-101
19. Live, D. H., Kumar, R. A., Beebe, X., and Danishefsky, S. J. (1996) Conformational influences of glycosylation of a peptide: A possible model for the effect of glycosylation on the rate of protein folding Proc. Natl. Acad. Sci. U.S.A. 93, 12759-12761 (Pubitemid 26382715)
20. O'Connor, S. E. and Imperiali, B. (1997) Conformational switching by asparagine-linked glycosylation J. Am. Chem. Soc. 119, 2295-2296 (Pubitemid 27160000)
21. Bosques, C. J., Tschampel, S. M., Woods, R. J., and Imperiali, B. (2004) Effects of glycosylation on peptide conformation: A synergistic experimental and computational study J. Am. Chem. Soc. 126, 8421-8425 (Pubitemid 38917964)
22. Hanson, S. R., Culyba, E. K., Hsu, T.-L., Wong, C.-H., Kelly, J. W., and Powers, E. T. (2009) The core trisaccharide of an N-linked glycoprotein intrinsically accelerates folding and enhances stability Proc. Natl. Acad. Sci. U.S.A. 106, 3131-3136
23. Wang, C., Eufemi, M., Turano, C., and Giartosio, A. (1996) Influence of the carbohydrate moiety on the stability of glycoproteins Biochemistry 35, 7299-7307 (Pubitemid 26189798)
24. Shental-Bechor, D. and Levy, Y. (2008) Effect of glycosylation on protein folding: A close look at thermodynamic stabilization Proc. Natl. Acad. Sci. U.S.A. 105, 8256-8261 (Pubitemid 351904743)
25. Culyba, E. K., Price, J. L., Hanson, S. R., Dhar, A., Wong, C. H., Gruebele, M., Powers, E. T., and Kelly, J. W. (2011) Protein native-state stabilization by placing aromatic side chains in N-glycosylated reverse turns Science 331, 571-575
26. Price, J. L., Powers, D. L., Powers, E. T., and Kelly, J. W. (2011) Glycosylation of the enhanced aromatic sequon is similarly stabilizing in three distinct reverse turn contexts Proc. Natl. Acad. Sci. U.S.A. 108, 14127-14132
27. Jäger, M., Dendle, M., and Kelly, J. W. (2009) Sequence determinants of thermodynamic stability in a WW domain-An all-β-sheet protein Protein Sci. 18, 1806-1813
28. Jäger, M., Deechongkit, S., Koepf, E. K., Nguyen, H., Gao, J., Powers, E. T., Gruebele, M., and Kelly, J. W. (2008) Understanding the mechanism of β-sheet folding from a chemical and biological perspective Biopolymers 90, 751-758
29. Ranganathan, R., Lu, K. P., Hunter, T., and Noel, J. P. (1997) Structural and functional analysis of the mitotic rotamase Pin1 suggests substrate recognition is phosphorylation dependent Cell 89, 875-886 (Pubitemid 27513514)
30. Price, J. L., Shental-Bechor, D., Dhar, A., Turner, M. J., Powers, E. T., Gruebele, M., Levy, Y., and Kelly, J. W. (2010) Context-dependent effects of asparagine glycosylation on Pin WW folding kinetics and thermodynamics J. Am. Chem. Soc. 132, 15359-15367