While thioesters are common intermediates in biochemical processes, they are much less appreciated in organic synthesis, also compared to other carboxylic acid derivatives. However, their chemistry and reactivity is intriguing and diversified, reaching much further than the acyl substitution and aldol chemistry. Herein, we focus on metal-catalyzed reactions for the synthesis of thioesters as well as their transformations. Reactions such as thiocarbonylation, cross-coupling, decarbonylation, allylic substitution or dual photoredox/metal catalysis are discussed. On one hand, new atom economic methods allow for convenient synthesis of thioesters from well available starting materials. On the other hand, various synthetically important compounds can by synthesized due to the multifaceted reactivity of thioesters that we aimed to depict.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201705025 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Cell Labeling with 15-YNE Is Useful for Tracking Protein Palmitoylation and Metabolic Lipid Flux in the Same Sample.
Molecules
January 2025
Goethe University Frankfurt, Institute of Clinical Pharmacology, Faculty of Medicine, Theodor Stern Kai 7, 60590 Frankfurt am Main, Germany.
Protein S-palmitoylation is the process by which a palmitoyl fatty acid is attached to a cysteine residue of a protein via a thioester bond. A range of methodologies are available for the detection of protein S-palmitoylation. In this study, two methods for the S-palmitoylation of different proteins were compared after metabolic labeling of cells with 15-hexadecynoic acid (15-YNE) to ascertain their relative usefulness.
View Article and Find Full Text PDFHomocysteine Metabolites, Endothelial Dysfunction, and Cardiovascular Disease.
Int J Mol Sci
January 2025
Department of Biochemistry and Biotechnology, Poznań University of Life Sciences, 60-632 Poznań, Poland.
Atherosclerosis is accompanied by inflammation that underlies cardiovascular disease (CVD) and its vascular manifestations, including acute stroke, myocardial infarction, and peripheral artery disease, the leading causes of morbidity/mortality worldwide. The monolayer of endothelial cells formed on the luminal surface of arteries and veins regulates vascular tone and permeability, which supports vascular homeostasis. Endothelial dysfunction, the first step in the development of atherosclerosis, is caused by mechanical and biochemical factors that disrupt vascular homeostasis and induce inflammation.
View Article and Find Full Text PDFUnveiling the Mechanisms of a Remission in Major Depressive Disorder (MDD)-like Syndrome: The Role of Hippocampal Palmitoyltransferase Expression and Stress Susceptibility.
Biomolecules
January 2025
Research and Education Resource Center, Peoples Friendship University of Russia (RUDN University), 117198 Moscow, Russia.
Post-translational modifications of proteins via palmitoylation, a thioester linkage of a 16-carbon fatty acid to a cysteine residue, reversibly increases their affinity for cholesterol-rich lipid rafts in membranes, changing their function. Little is known about how altered palmitoylation affects function at the systemic level and contributes to CNS pathology. However, recent studies suggested a role for the downregulation of palmitoyl acetyltransferase (DHHC) 21 gene expression in the development of Major Depressive Disorder (MDD)-like syndrome.
View Article and Find Full Text PDFReview on the o-aminoaniline Moiety in Peptide and Protein Chemistry.
Chembiochem
January 2025
University of Wisconsin-Madison, Pharmacy, 777 Highland Ave, 53705, Madison, UNITED STATES OF AMERICA.
Peptides and proteins are important functional biomolecules both inside and outside of living organisms. The ability to prepare various types of functionalized peptides and proteins is essential for understanding fundamental biological processes, such as protein folding and post-translational modifications (PTMs), and for developing new therapeutics for many diseases, such as cancers and neurodegenerative diseases. The o-aminoaniline moiety was first proposed for activation to a thioester precursor and used for native chemical ligation to prepare large peptides and proteins.
View Article and Find Full Text PDFChemical Logic of Peptide Branching by Iterative Nonlinear Nonribosomal Peptide Synthetases.
Biochemistry
January 2025
Department of Chemistry, Washington University in St. Louis, One Brookings Drive, St. Louis, Missouri 63130, United States.
Branch-point syntheses in nonribosomal peptide assembly are rare but useful strategies to generate tripodal peptides with advantageous hexadentate iron-chelating capabilities, as seen in siderophores. However, the chemical logic underlying the peptide branching by nonribosomal peptide synthetase (NRPS) often remains complex and elusive. Here, we review the common strategies for the biosynthesis of branched nonribosomal peptides (NRPs) and present our biochemical investigation on the NRPS-catalyzed assembly of fimsbactin A, a branched mixed-ligand siderophore produced by the human pathogenic strain .
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!