Proline Analogues
V Kubyshkin, M Rubini - Chemical Reviews, 2024 - ACS Publications
Within the canonical repertoire of the amino acid involved in protein biogenesis, proline
plays a unique role as an amino acid presenting a modified backbone rather than a side …
plays a unique role as an amino acid presenting a modified backbone rather than a side …
Natural and synthetic halogenated amino acids—Structural and bioactive features in antimicrobial peptides and peptidomimetics
The 3D structure and surface characteristics of proteins and peptides are crucial for
interactions with receptors or ligands and can be modified to some extent to modulate their …
interactions with receptors or ligands and can be modified to some extent to modulate their …
3-Fluoro-4-hydroxyprolines: synthesis, conformational analysis, and stereoselective recognition by the VHL E3 ubiquitin ligase for targeted protein degradation
Hydroxylation and fluorination of proline alters the pyrrolidine ring pucker and the trans: cis
amide bond ratio in a stereochemistry-dependent fashion, affecting molecular recognition of …
amide bond ratio in a stereochemistry-dependent fashion, affecting molecular recognition of …
Perfluorocarbons in chemical biology
MA Miller, EM Sletten - ChemBioChem, 2020 - Wiley Online Library
Perfluorocarbons, saturated carbon chains in which all the hydrogen atoms are replaced
with fluorine, form a separate phase from both organic and aqueous solutions. Though …
with fluorine, form a separate phase from both organic and aqueous solutions. Though …
Entropic contribution of elongation factor P to proline positioning at the catalytic center of the ribosome
LK Doerfel, I Wohlgemuth, V Kubyshkin… - Journal of the …, 2015 - ACS Publications
The peptide bond formation with the amino acid proline (Pro) on the ribosome is slow,
resulting in translational stalling when several Pro have to be incorporated into the peptide …
resulting in translational stalling when several Pro have to be incorporated into the peptide …
Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains
SA Miles, JA Nillama, L Hunter - Molecules, 2023 - mdpi.com
Side chain-fluorinated amino acids are useful tools in medicinal chemistry and protein
science. In this review, we outline some general strategies for incorporating fluorine atom (s) …
science. In this review, we outline some general strategies for incorporating fluorine atom (s) …
Fluorinated prolines as conformational tools and reporters for peptide and protein chemistry
SJM Verhoork, PM Killoran, CR Coxon - Biochemistry, 2018 - ACS Publications
Amide bonds at the proline nitrogen are particularly susceptible to rotation, affording cis and
trans isomers. Installation of a stereochemically defined electron-withdrawing fluorine atom …
trans isomers. Installation of a stereochemically defined electron-withdrawing fluorine atom …
Synthesis of spirocyclic pyrrolidines: Advanced building blocks for drug discovery
BA Chalyk, MV Butko, OO Yanshyna… - … A European Journal, 2017 - Wiley Online Library
In the context of drug discovery, novel spirocyclic pyrrolidines have been synthesized in two
steps from common three‐to seven‐membered‐ring (hetero) alicyclic ketones. The key …
steps from common three‐to seven‐membered‐ring (hetero) alicyclic ketones. The key …
Fluorinated peptide biomaterials
Fluorinated compounds, while rarely used by nature, are emerging as fundamental
ingredients in biomedical research, with applications in drug discovery, metabolomics …
ingredients in biomedical research, with applications in drug discovery, metabolomics …
1‐Substituted 2‐Azaspiro [3.3] heptanes: Overlooked Motifs for Drug Discovery
AA Kirichok, I Shton, M Kliachyna, I Pishel… - Angewandte …, 2017 - Wiley Online Library
The 2‐substituted piperidine core is found in drugs (18 FDA‐approved drugs), however,
their spirocyclic analogues remain unknown. Described here is the synthesis of spirocyclic …
their spirocyclic analogues remain unknown. Described here is the synthesis of spirocyclic …