Computational study of glucosepane–water and hydrogen bond formation: an electron topology and orbital analysis

References

• Alecu, I. M. , Zheng, J. , Zhao, Y. , & Truhlar, D. G. (2010). Computational thermochemistry: Scale factor database and scale factors for vibrational frequencies obtained from electronic model chemistries. Journal of Chemical Theory and Computation , 6 , 2872–2887.10.1021/ct100326h
   PubMed Web of Science ®Google Scholar
• Avery, N. C., & Bailey, A. J. (2005). Enzymic and non-enzymic cross-linking mechanisms in relation to turnover of collagen: Relevance to aging and exercise. Scandinavian Journal of Medicine and Science in Sports , 15 , 231–240.10.1111/sms.2005.15.issue-4
   PubMed Web of Science ®Google Scholar
• Avery, N. C., & Bailey, A. J. (2006). The effects of the Maillard reaction on the physical properties and cell interactions of collagen. Pathologie Biologie , 54 , 387–395.10.1016/j.patbio.2006.07.005
   PubMed Web of Science ®Google Scholar
• Bader, R. F. W. (1991). A quantum theory of molecular structure and its applications. Chemical Reviews , 91 , 893–928.10.1021/cr00005a013
   Web of Science ®Google Scholar
• Bader, R. F. E., & Essén, H. J. (1984). The characterization of atomic interactions. Chem Phys , 80 , 1943–1960.
   Web of Science ®Google Scholar
• Bhattacharjee, A., & Bansal, M. (2005). Collagen Structure: The Madras Triple Helix and the Current Scenario. IUBMB Life (International Union of Biochemistry and Molecular Biology: Life) , 57 , 161–172.10.1080/15216540500090710
   Google Scholar
• Bulterijs, S., & Sjöberg, J. S. (2009). Characteristics, formation and pathophysiology of glucosepane, a major advanced glycation end product. Rejuvenation Res , 12 , 137–148.
   PubMed Web of Science ®Google Scholar
• Çarçabal, P. , Jockusch, R. A. , Hünih, I. , Snoek, L. C. , Kroemer, R. T. , Davis, B. G. , … Simons, J. P. (2005). Hydrogen bonding and cooperativity in isolated and hydrated sugars: Mannose, galactose, glucose and lactose. Journal of the American Chemical Society , 127 , 11414–11425.
   PubMed Web of Science ®Google Scholar
• Chai, J. D., & Head-Gordon, M. (2008). Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Physical Chemistry Chemical Physics , 10 , 6615–6620.10.1039/b810189b
   PubMed Web of Science ®Google Scholar
• Collier, T. , Nash, A. , Birch, H. L. , & de Leeuw, N. H. (2015). Preferential sites for intramolecular glucosepane cross-link formation in type I collagen: A thermodynamic study. Matrix Biology , 48 , 78–88.10.1016/j.matbio.2015.06.001
   PubMed Web of Science ®Google Scholar
• Frisch, M. J. , Trucks, G. W. , Schlegel, H. B. , Scuseria, G. E. , Robb, M. A. , Cheeseman, J. R. , … Fox, D. J. (2010) Gaussian 09, Revision B.01, Gaussian Inc, Wallingford CT.
   Google Scholar
• Hanwell, M. D. , Curtis, D. E. , Lonie, D. C. , Vandermeersch, T. , Zurek, E. , & Hutchison, G. R. (2012). Avogadro: An advanced semantic chemical editors, visualization, and analysis platform. Journal of Cheminformatics , 4 , 17.10.1186/1758-2946-4-17
   PubMed Web of Science ®Google Scholar
• Kent, M. J. , Light, N. D. , & Bailey, A. J. (1985). Evidence for glucose-mediated covalent cross-linking of collagen after glycosylation in vitro . Biochemical Journal , 225 , 745–752.10.1042/bj2250745
   PubMed Web of Science ®Google Scholar
• Klopper, P. J. (1986). Collagen in surgical research. European Surgical Research , 18 , 218–223.10.1159/000128529
   PubMed Web of Science ®Google Scholar
• Lane, J. R. , Contreras-García, J. , Piquemal, J.-P. , Miller, B. J. , & Kjaergaard, H. G. (2013). Are bond critical points really critical for hydrogen bonding? Journal of Chemical Theory and Computation , 9 , 3263–3266.10.1021/ct400420r
   PubMed Web of Science ®Google Scholar
• Lu, T., & Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyser. Journal of Computational Chemistry , 33 , 580–592.10.1002/jcc.v33.5
   PubMed Web of Science ®Google Scholar
• Maillard, L. C. (1913). Genèse des Matieres Protéiques et des Matieres Humiques: Action de la Glycérine et des Sugres sur les Acides α- amines[Genesis of protean and humic materials: Action of glycerine and sugars on α-amino acids], C. R de la Société de Biologie , Masson & Cie, Paris.
   Google Scholar
• Maroudas, A. , Palla, G. , & Gilav, E. (1992). Racemization of aspartic acid in human articular cartilage. Connective Tissue Research , 28 , 161–169.10.3109/03008209209015033
   PubMed Web of Science ®Google Scholar
• Møller, C., & Plesset, M. S. (1934). Note on an approximation treatment for many-electron systems. Physical Review , 46 , 618–622.10.1103/PhysRev.46.618
   Web of Science ®Google Scholar
• Nomoto, K. , Yagi, M. , Hamada, U. , Naito, J. , & Yonei, Y. (2013). Identification of advanced glycation endproducts derived fluorescence spectrum in vitro and human skin. Anti-Aging Medicine , 10 , 92–100.
   Google Scholar
• Ottani, V. , Raspanti, M. , & Ruggeri, A. (2001). Collagen structure and functional implications. Micron , 32 , 251–260.10.1016/S0968-4328(00)00042-1
   PubMed Web of Science ®Google Scholar
• Pimentel, G. C., & McClellan, A. L. (1960). The hydrogen bond . San Francisco: Freeman.
   Google Scholar
• Rich, H. , Odlyha, M. , Cheema, U. , Mudera, V. , & Bozec, L. (2014). Effects of photochemical riboflavin-mediated crosslinks on the physical properties of collagen constructs and fibrils. Journal of Materials Science: Materials in Medicine , 25 , 11–21.10.1007/s10856-013-5038-7
   PubMed Web of Science ®Google Scholar
• Sell, D. R. , Biemel, K. M. , Reihl, O. , Lederer, M. O. , Strauch, C. M. , & Monnier, V. M. (2005). Glucosepane is a major protein cross-link of the senescent human extracellular matrix. Relationship with diabetes. Journal of Biological Chemistry , 280 , 12310–12315.
   PubMed Web of Science ®Google Scholar
• Silla, J. M. , Cormanich, R. A. , Rittner, R. , & Freitas, M. P. (2014). Does intramolecular hydrogen bond play a key role in the stereochemistry of α- and β-d-glucose? Carbohydrate Research , 396 , 9–13.10.1016/j.carres.2014.06.013
   PubMed Web of Science ®Google Scholar
• Steiner, T. (2002). The Hydrogen Bond in the Solid State. Angewandte Chemie International Edition , 41 , 48–76.10.1002/1521-3773(20020104)41:1<>1.0.CO;2-5
   Web of Science ®Google Scholar
• Thorpe, C. T. , Streeter, I. , Pinchbeck, G. L. , Goodship, A. E. , Clegg, P. D. , & Birch, H. L. (2010). Aspartic acid racemization and collagen degradation markers reveal an accumulation of damage in tendon collagen that is enhanced with aging. Journal of Biological Chemistry , 285 , 15674–15681.10.1074/jbc.M109.077503
   PubMed Web of Science ®Google Scholar