Potent thioester and thiol inhibitors of IMP-1 metallo-beta-lactamase have been synthesized employing a solid-phase Mitsunobu reaction as the key step.
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http://dx.doi.org/10.1016/s0960-894x(99)00425-4 | DOI Listing |
RSC Adv
December 2024
Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Quimica, Universidad de la República Gral Flores 2124 Montevideo 11800 Uruguay
A new series of chiral δ-thiolactone derivatives have been prepared. These compounds exemplify the acetalic N-C-S reversibility of fused thiazolidines toward the thermodynamic product. The stereochemistry of the synthesized compounds was elucidated using X-ray crystallography, NOESY spectroscopy, and DFT calculations.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Department of Chemistry, New York University, New York, New York 10003, USA.
We report the use of unprotected amino acids as submonomer reagents in the solid-phase synthesis of -substituted glycine peptoid oligomers. Subsequent coupling of an amine, alcohol, or thiol to the free carboxylate of the incorporated amino acid provides access to peptoids bearing amides, esters, and thioesters as side chain pendant groups and permits further elongation of the peptoid backbone. The palette of readily obtained building blocks suitable for solid-phase peptoid synthesis is substantially expanded through this protocol, further enhancing the chemical diversity and potential applications of sequence-specific peptoid oligomers.
View Article and Find Full Text PDFNucleic Acids Res
December 2024
Malopolska Centre of Biotechnology (MCB), Jagiellonian University, Gronostajowa7a, 30-387 Krakow, Poland.
Ubiquitin-related modifier 1 (Urm1) is a highly conserved member of the ubiquitin-like (UBL) family of proteins. Urm1 is a key component of the eukaryotic transfer RNA (tRNA) thiolation cascade, responsible for introducing sulfur at wobble uridine (U34) in several eukaryotic tRNAs. Urm1 must be thiocarboxylated (Urm1-SH) by its E1 activating enzyme UBL protein activator 4 (Uba4).
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
December 2024
Department of Pharmacy, Musashino University.
This study introduces a novel method for ring-closing chlorosulfenylation of alkenoic thioesters using N-chlorosuccinimide in hexafluoroisopropanol under mild conditions. This reaction efficiently forms five-membered cyclic sulfur compounds with high selectivity, representing a significant advancement in the synthesis of chlorinated S-heterocycles. Computational analysis using density functional theory demonstrates the superiority of thioester nucleophiles over traditional benzyl sulfides in this reaction, highlighting the energetic preference for thioesters.
View Article and Find Full Text PDFJACS Au
November 2024
Institute for Advanced Chemistry of Catalonia (IQAC), Spanish National Research Council (CSIC), C/ Jordi Girona 18-26, 08034 Barcelona, Spain.
Native chemical ligation (NCL) ligates two unprotected peptides in an aqueous buffer. One of the fragments features a C-terminal α-thioester functional group, and the second bears an N-terminal cysteine. The reaction mechanism depicts two steps: an intermolecular thiol-thioester exchange resulting in a transient thioester, followed by an intramolecular acyl shift to yield the final native peptide bond.
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