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- W2894615210 abstract "β-Strands are formed by extended linear peptide chains that are usually paired to form β-sheet structure through interstrand hydrogen bonding. Linking a structured organic molecule with α-amino acid(s) can enforce or stabilize β-strand-like extended structures of the jointed amino acids. Spectroscopic and simulation studies indicated that the presence of a C-terminal 7-azabicyclo[2.2.1]heptane amine (Abh) favors a β-strand-like extended conformation of the adjacent α-amino acid on the N side. The bridgehead substitution of the Abh unit biases the amide cis–trans equilibrium of the adjacent α-amino acid residue to cis conformation. The proximity, specified by the presence of bond paths (such as H–H bond path) between the bridgehead proton of Abh and the α-proton of the α-amino acid provides a driving force favoring the extended conformation, which is independent of solvents. These results provide a basis for de novo design of β-strand-mimicking extended peptides by using β-strand enforcer/stabilizer even in the absence of the interstrand hydrogen bonding." @default.
- W2894615210 created "2018-10-12" @default.
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- W2894615210 date "2018-10-04" @default.
- W2894615210 modified "2023-10-14" @default.
- W2894615210 title "Application of C-Terminal 7-Azabicyclo[2.2.1]heptane to Stabilize β-Strand-like Extended Conformation of a Neighboring α-Amino Acid" @default.
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- W2894615210 doi "https://doi.org/10.1021/acs.joc.8b01756" @default.
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