Observation of a unique pattern of bifurcated hydrogen bonds in the crystal structures of the N-glycoprotein linkage region models

Glycobiology

Volumn 16, Issue 4, 2006, Pages 343-348

  Loganathan, Duraikkannu ^a   Aich, Udayanath ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

C H...O interactions; Carbohydrates; H bonding; N glycoprotein models and analogs; X ray diffraction

Indexed keywords

GLYCOPROTEIN; N GLYCOPROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN FOLDING; PROTEIN STABILITY; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; GLYCOPROTEINS; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; PROTEIN STRUCTURE, SECONDARY;

EID: 33645109741     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwj070     Document Type: Article

References (20)

1. Aich, U., Lakshmanan, T., Varghese, B., and Loganathan, D. (2003) Crystal structure of β-1-N-cholaracetamido derivatives of D-glucose and D-galactose. J. Carbohydr. Chem., 22, 891-901.
2. Bush, C.A., Blumberg, K., and Brown, J.N. (1982) Crystal structure and solution conformation of, 1-N-acetyl-beta-D-glucopyranosyl amine: A model for the glycopeptide linkage. Biopolymers, 21, 1971-1977.
3. Delbaere, L.T.J. (1974) The molecular and crystal structures of, 4-N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine trihydrate and 4-N-(beta-D-glucopyranosyl)-L-asparagine monohydrate. The X-ray analysis of a carbohydrate-peptide linkage. Biochem. J., 143, 197-205.
4. Derewenda, S.Z., Lee, L., and Derewenda, U. (1995) The occurrence of C-H...O hydrogen bonds in proteins. J. Mol. Biol., 252, 248-262.
5. Desiraju, G.R. and Steiner, T. (1999) The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press, New York.
6. Erbel, P.J., Karimi-Nejad, Y., van Kuik, J.A., Boelens, R., Kamerling, J.P., and Vliegenthart, J.F.G. (2000) Effects of the N-linked glycans on the 3D structure of the free α-subunit of human chorionic gonadotropin. Biochemistry, 39, 6012-6021.
7. Imberty, A. and Perez, S. (1995) Stereochemistry of the N-glycosylation sites in glycoproteins. Protein Eng., 8, 699-709.
8. Jeffrey, G.A. and Saenger, W. (1991) Hydrogen Bonding in Biological Structures. Springer-Verlag, New York.
9. Lakshmanan, T. and Loganathan, D. (2001) β-1-N-Acetamido-(4-O-β-D-galactopyranosyl)-D-glucopyranose dihydrate. Acta Crystallogr. C, C57, 825-826.
10. Lakshmanan, T., Sriram, D., Priya, K., and Loganathan, D. (2003) On the structural significance of the linkage region constituents of N-glycoproteins: An X-ray crystallographic investigation using models and analogs. Biochem. Biophys. Res. Commun, 312, 405-413.
11. Ohenassien, J., Avenel, D., Neuman, A., and Giller-Pandraud, H.G. (1980) Structure cristalline de la 2-acetamido-1-N-(L-aspart-4-oyl)-2-desoxy-β-D-glucopyranosylamine. Carbohydr. Res., 80, 1-13.
12. Peluso, S., Ufret, M.L., O'Reilly, M.K., and Imperiali, B. (2002) Neoglycopeptides as inhibitors of oligosaccharyl transferase: Insight into negotiating product inhibition. Chem. Biol., 9, 1323-1328.
13. Petrescu, A.J., Milac, A.L., Petrescu, S.M., Dwek, R.A., and Wormald, M.R. (2004) Statistical analysis of the protein environment of N-glycosylation sites: Implications for occupancy, structure, and folding. Glycobiology, 14, 103-114.
14. Spiro, R.J. (2002) Protein glycosylation: Nature, distribution, enzymatic formation, and disease implications of glycopeptide bonds. Glycobiology, 12, 43R-56R.
15. Sriram, D., Lakshmanan, T., Loganathan, D., and Srinivasan, S. (1998) Crystal structure of a hydrated N-glycoprotein linkage region model and its analogue: Hydrogen bonding and Pi-Pi stacking driven molecular assembly. Carbohydr. Res., 309, 227-236.
16. Sriram, D., Srinivasan, S., Priya, K., Aruna, V., and Loganathan, D. (1998) β-1-N-benzamido-D-glucopyranose. Acta Crystallogr. C, C54, 1670-1672.
17. Sriram, D., Srinivasan, H., Srinivasan, S., Priya, K., Vishnu Thirtha, M., and Loganathan, D. (1997) β-1-N-acetamido-D-glucopynanose. Acta Crystallogr. C, C53, 1075-1077.
18. Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., and Marth, J. (1999) Essentials of Glycobiology. Cold Spring Harbor Laboratories press, Cold Spring Harbor, New York.
19. Wahl, M.C. and Sundaralingam, M. (1997) C-H...O hydrogen bonding in biology. Trends Biochem. Sci., 22, 97-102.
20. Wyss, D.F., Choi, J.S., Li, J., Knoppers, M.H., Willis, K.J., Arulanandam, A.R., Smolyar, A., Reinherz, E.L., and Wagner, G. (1995) CHO structure, conformation and function of the N-linked glycan in the adhesion domain of human CD2. Science, 269, 1273-1278.