What are typical modifications in peptidomimetic design? Describe three examples.
For what purposes can artificial amino acids be used?
What backbone modifications are there and what consequence do they have?
depsi, thiodepsi, ketmethylene: enhanced rotational freedom
aza: loss of stereochemistry
alpha-alkylation: crowded C
What are secondary structure mimetics?
mimetic of alpha-helices, beta-sheets and turns in between
Turns
macrocycles
beta-/gamma-turn
as long as angle and geometry are the same, the exact chemistry does not matter
often, you need N- and C-terminus anyway to connect turn to the rest of the peptide
Beta-sheet mimetics
completely artificial beta-sheet constructions can be used to build channels (not accessible to enzymes, impossible to decompose by the cell)
Alpha-helix mimetics
Name scaffold mimetics approaches.
phenylic scaffolds
alpha-helix mimic (2 turns)
heterocyclic scaffolds
H-bond guided scaffolds
What are foldamers and what kinds of foldamers do you know?
Foldamers: protein mimetics with alternative folding
Beta- and gamma-peptides - differently sized helices
Peptoids
Last changed9 months ago
