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 …

Azapeptides and their therapeutic potential

C Proulx, D Sabatino, R Hopewell… - Future medicinal …, 2011 - Taylor & Francis
Azapeptides are peptide analogs in which one or more of the amino residues is replaced by
a semicarbazide. This substitution of a nitrogen for the α-carbon center results in …

Back to the future: ribonuclease A

GR Marshall, JA Feng, DJ Kuster - Peptide Science, 2008 - Wiley Online Library
Abstract Pancreatic ribonuclease A (EC 3.1. 27.5, RNase) is, perhaps, the best‐studied
enzyme of the 20th century. It was isolated by René Dubos, crystallized by Moses Kunitz …

Electronic control of amide cis− trans isomerism via the aromatic− prolyl interaction

KM Thomas, D Naduthambi… - Journal of the American …, 2006 - ACS Publications
The cis− trans isomerization of prolyl amide bonds results in large structural and functional
changes in proteins and is a rate-determining step in protein folding. We describe a novel …

β-Turn editing in Gramicidin S: Activity impact on replacing proline α-carbon with stereodynamic nitrogen

J Lal, G Kaul, A Akhir, D Saxena, H Dubkara… - Bioorganic …, 2023 - Elsevier
Gramicidin S, natural antimicrobial peptide is used commercially in medicinal lozenges for
sore throat and Gram-negative and Gram-positive bacterial infections. However, its clinical …

Influence of proline chirality on neighbouring azaproline residue stereodynamic nitrogen preorganization

J Lal, G Prajapati, R Meena, R Kant… - Chemistry–An Asian …, 2023 - Wiley Online Library
We report herein the first systematic crystal structural investigation of azaproline
incorporated in homo‐and heterochiral diprolyl peptides. The X‐ray crystallography data of …

Development of small molecules designed to modulate protein–protein interactions

Y Che, BR Brooks, GR Marshall - Journal of computer-aided molecular …, 2006 - Springer
Protein–protein interactions are ubiquitous, essential to almost all known biological
processes, and offer attractive opportunities for therapeutic intervention. Developing small …

[HTML][HTML] Theoretical structure determination of a class of heterocyclic compounds: The pyrazolidines

I Alkorta, J Elguero - Chemical Physics Letters, 2024 - Elsevier
Theoretical calculations at the B3LYP-D3 (BJ)/6–311++ G (d, p) level of a series of 35
neutral pyrazolidines and 3 protonated derivatives have been carried out for different …

Engineering cyclic tetrapeptides containing chimeric amino acids as preferred reverse-turn scaffolds

Y Che, GR Marshall - Journal of medicinal chemistry, 2006 - ACS Publications
Four residues making almost a complete 180° turn in the direction of the peptide chain
define a reverse turn, a common motif and recognition site in proteins. Cyclization between …

[PDF][PDF] Conformational properties of 4-mercaptoproline and related derivatives

SA Cadamuro, R Reichold, U Kusebauch… - … EDITION IN ENGLISH …, 2008 - academia.edu
Proline residues have long been recognized to play a unique and important role in the
structural properties of peptides and proteins. The cis/trans isomerization of the aminoacyl …