Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Дек. 30, 2024
Chiral α-amino nitriles, derived from their canonical acids, can be attached to the peptide C-terminus and undergo biocompatible cyclisation with an N-terminal cysteine residue, yielding macrocyclic thiazole peptides after mild oxidation.
Язык: Английский
Chemical Science, Год журнала: 2024, Номер 15(7), С. 2300 - 2322
Опубликована: Янв. 1, 2024
The identification of macrocyclic peptides in drug discovery demands not only advanced screening strategies but also robust and reliable synthetic methodologies to constrain under biocompatible conditions.
Язык: Английский
Процитировано
22
Encyclopedia of Reagents for Organic Synthesis, Год журнала: 2025, Номер unknown, С. 1 - 2
Опубликована: Янв. 3, 2025
image [2968514‐49‐8] C 7 H 2 FN 3 (MW 147.11) InChI = 1S/C7H2FN3/c8‐5‐1‐6(3‐9)11‐7(2‐5)4‐10/h1‐2H InChIKey OYXYUVMEIMAJAW‐UHFFFAOYSA‐N (electrophilic reagent for the facile preparation of 2,6‐dicyanopyridine‐substituted side chains in amino acids, peptides, and proteins) Alternative Names: 4‐fluoropyridine‐2,6‐dicarbonitrile (IUPAC), 4F‐DCP, FDCP. Physical Data: mp 101 °C. Solubility: soluble acetone, CH Cl , CHCl DMF, DMSO, Et O, EtOAc, MeCN, MeOH, PhCH THF; insoluble n ‐hexane, ‐heptane. Form Supplied in: white crystalline solid. Analysis Reagent Purity: NMR, GC‐MS, IR. Preparative Methods: nucleophilic aromatic substitution 4‐chloropyridine‐2,6‐dicarbonitrile CsF DMSO at high temperature. Purification: liquid–liquid extraction followed by silica flash column chromatography. Handling, Storage, Precautions: refrigerate solid; toxicity unknown.
Язык: Английский
Процитировано
1
Chemical Communications, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
A small molecular adapter enables site-specific peptide–protein conjugation via cysteine modification and cyanopyridine–aminothiol reactions, yielding complex branched or cyclic architectures for potential protein therapeutics.
Язык: Английский
Процитировано
0
Macromolecular Rapid Communications, Год журнала: 2024, Номер unknown
Опубликована: Окт. 22, 2024
Abstract Protein function results from the precise folding of polypeptides into bespoke architectures. Taking inspiration nature, field single‐chain nanoparticles (SCNPs), intramolecularly crosslinked synthetic polymers, emerged. In contrast to SCNPs is generally defined by parent polymer or applied crosslinker, rather than crosslinking process itself. This work explores cyanopyridine–aminothiol click reaction crosslink peptide‐decorated polymers intra‐macromolecularly endow resulting with emerging functionality, conversion N‐terminal cysteine units pyridine‐thiazolines. Dimethylacrylamide based different cysteine‐terminated amino acid sequences tethered their sidechains are investigated ( P1 (C), P2 (GDHC), P3 (GDSC)) and SCNPs. Since deprotection yields disulfide‐based SCNPs, a direct comparison between disulfide pyridine‐thiazolines possible. revealed two properties pyridine‐thiazoline SCNPs: 1) The formation gave rise metal binding sites within SCNP, which complexed iron. 2) Depending on peptide sequence in precursor polymer, hydrolytic activity either increased (GDHC) decreased (GDSC) upon compared identical crosslinks.
Язык: Английский
Процитировано
0
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Дек. 30, 2024
Chiral α-amino nitriles, derived from their canonical acids, can be attached to the peptide C-terminus and undergo biocompatible cyclisation with an N-terminal cysteine residue, yielding macrocyclic thiazole peptides after mild oxidation.
Язык: Английский
Процитировано
0