Affiliation:
1. Department of Chemistry and Biochemistry, DePaul University, Chicago, IL 60614, USA
Abstract
DFT calculations were carried out to examine geometries and binding energies of H-bond-driven peptide nanotubes. A bolaamphiphile molecule, consisting of two N-α amido glycylglycine head groups linked by either one CH2 group or seven CH2 groups, is used as a building block for nanotube self-assembly. In addition to hydrogen bonds between adjacent carboxy or amide groups, nanotube formation is also driven by weak C-H· · ·O hydrogen bonds between a methylene group and the carboxy OH group, and between a methylene group and an amide O=C group. The intratubular O-H· · ·O=C hydrogen bonds account for approximately a third of the binding energies. Binding energies calculated with the wB97XD/DGDZVP method show that the hydrocarbon chains play a stabilizing role in nanotube self-assembly. The shortest nanotube has the length of a single monomer and a diameter than increases with the number of monomers. Lengthening of the tubular structure occurs through intertubular O-H· · ·O=C hydrogen bonds. The average intertubular O-H· · ·O=C hydrogen bond binding energy is estimated to change with the size of the nanotubes, decreasing slightly towards some plateau value near 15 kcal/mol according to the wB97XD/DGDZVP method.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference111 articles.
1. Polarity and ionization from the standpoint of the Lewis theory of valence;Latimer;J. Am. Chem. Soc.,1920
2. Gilli, P., and Gilli, G. (2009). The Nature of the Hydrogen Bond, Oxford University Press.
3. Desiraju, G.R., and Steiner, T. (1999). The Weak Hydrogen Bond, Oxford University Press.
4. Jeffrey, G.A. (1997). An Introduction to Hydrogen Bonding, Oxford University Press.
5. Scheiner, S. (1997). Hydrogen Bonding: A Theoretical Perspective, Oxford University Press.
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