Cyclization configurations

The primary ligation approaches to synthesize lactam cyclic peptides are
head-to-tail, side-chain-to-side-chain, head-to-side-chain, and side-chain-to-tail,
depending on the location of the functional groups within the peptide sequence.

  • Occurs between N-terminus to C-terminus.
  • Via Amide bond formation (lactamization).
  • Most frequently used cyclization conferring greater stability. 

Occurs between N-terminus and an internal COOH
(e.g. the ß-COOH-group of Asp or γ-COOH-group of Glu).

Occurs between internal NH2s and C-terminus
(e.g. the ε-NH2–group of Lys).

Occurs between Side chain of Lysine (ε-NH2–group of Lys)
to Aspartic or Glutamic acid (γ-COOH-group).

Featured Citations

Head‐to‐Tail Cyclic Peptide Inhibitors of the Interaction between Human von Willebrand Factor and Collagen.

The study examined novel cyclic peptides as moderate inhibitors of the protein–protein interaction between von Willebrand factor (vWF) and collagen that initiates blood clot formation.

‘All of the head‐to‐tail cyclic peptides, was purchased and synthesized by AnaSpec (Eurogentec's US subsidiary).‘

Other constrained peptides