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- Title
An Efficient, Site‐Selective and Spontaneous Peptide Macrocyclisation During in vitro Translation.
- Authors
Liu, Minglong; Yoshisada, Ryoji; Amedi, Avand; Hopstaken, Antonius J. P.; Pascha, Mirte N.; de Haan, Cornelis A. M.; Geerke, Daan P.; Poole, David A.; Jongkees, Seino A. K.
- Abstract
Macrocyclisation provides a means of stabilising the conformation of peptides, often resulting in improved stability, selectivity, affinity, and cell permeability. In this work, a new approach to peptide macrocyclisation is reported, using a cyanobenzothiazole‐containing amino acid that can be incorporated into peptides by both in vitro translation and solid phase peptide synthesis, meaning it should be applicable to peptide discovery by mRNA display. This cyclisation proceeds rapidly, with minimal by‐products, is selective over other amino acids including non N‐terminal cysteines, and is compatible with further peptide elaboration exploiting such an additional cysteine in bicyclisation and derivatisation reactions. Molecular dynamics simulations show that the new cyclisation group is likely to influence the peptide conformation as compared to previous thioether‐based approaches, through rigidity and intramolecular aromatic interactions, illustrating their complementarity.
- Subjects
PEPTIDES; MOLECULAR dynamics; PEPTIDE synthesis; INTRAMOLECULAR forces; CELL permeability
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 14, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202203923