Organic Catalysts and Ligands Derived from Amino Acids and Peptides DOI

Lipat Kaur,

Karuna Thakare,

Aman Singh Barahdia

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134671 - 134671

Published: April 1, 2025

Language: Английский

From lead to market: chemical approaches to transform peptides into therapeutics DOI
Caitlin L. Gare, Andrew M. White, Lara R. Malins

et al.

Trends in Biochemical Sciences, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 1, 2025

Language: Английский

Citations

2
Ex Situ Synthesis of N-Capped Peptides in the Solution Phase via Palladium-Catalyzed Aminocarbonylation Utilizing Chloroform-COware DOI
Aman Singh Barahdia,

Karuna Thakare,

Rahul Jain

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

We report the synthesis of N-capped peptides under mild conditions using oxidative aminocarbonylation aryl iodides and peptide esters as nucleophiles in solution phase. Ex situ chloroform chamber A generates CO, which diffuses to B, contains other reactants. This method offers at 80 °C for 12 h. synthesized 36 this method, including an anticancer drug bortezomib analogue, with isolated yield ranging from 52 91%. The present gives easy access previously inaccessible N-capping groups, heteroaromatic ring-capped enable robust analogue designs peptide-based discovery.

Language: Английский

Citations

1
Identification of constrained peptidomimetics carrying a Michael acceptor warhead as antitrypanosomal agents DOI Creative Commons
Santo Previti, Elsa Calcaterra, Carla Di Chio

et al.

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 288, P. 117389 - 117389

Published: Feb. 12, 2025

In this structure-activity relationship (SAR) study, we report the development of rhodesain-targeting peptidomimetics with antitrypanosomal activity. The new compounds (SPR65-SPR80) feature 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) moiety as conformationally constrained Phe analog. Various substituents were inserted at P1 and P3 positions, methyl vinyl ketone was introduced warhead. incorporation Tic resulted in reduced affinity against rhodesain compared to parent containing (2a-m), suggesting that its rigidity negatively affects target binding. Nevertheless, promising EC50 values ranging from 0.42 1.35 μM observed cell-based assays, probably due better pharmacokinetic properties and/or interactions additional protozoal targets. CC50 > 100 observed. Therefore, while is less tolerated by rhodesain, peptidomimetic Michael acceptors led effects comparable or slightly than those no cytotoxicity up μM. These findings could be taken into consideration future SAR studies aimed agents.

Language: Английский

Citations

0
Expanding the Scope of Azole-Based γ-Amino Acids DOI
Ludovic T. Maillard,

Samantha Chaise,

Audrey Gacogne

et al.

Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

Abstract The development of non-canonical amino acids is pivotal to peptide engineering, enabling the design molecules with novel structural features, improved activities, and optimized metabolic profiles. Among these, heteroaromatic γ-amino have attracted significant attention for their ability mimic native folds while accessing conformational spaces. In this study, chemical diversity was expanded by introducing two new monomers, ATC* AOC*, designed around a thiazole an oxazole scaffold, respectively. These analogues, characterized tunable substitution patterns precise stereochemical control significantly expand well-established ATC family.

Language: Английский

Citations

0
Organic Catalysts and Ligands Derived from Amino Acids and Peptides DOI

Lipat Kaur,

Karuna Thakare,

Aman Singh Barahdia

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134671 - 134671

Published: April 1, 2025

Language: Английский

Citations

0