AI Article Synopsis
- Labeling proteins naturally with fluorescent tags can disrupt their functions due to the bulkiness of existing methods.
- This study introduces a two-step method to attach fluorescent probes to a small 13-amino-acid peptide using enzyme-mediated labeling and palladium-catalyzed Sonogashira cross-coupling.
- The approach utilizes p-iodophenyl derivatives to create a reactive site on the peptide, allowing for selective attachment of fluorophores while minimizing interference with natural protein functions.
Article Abstract
Labeling proteins in their natural settings with fluorescent proteins or protein tags often leads to problems. Despite the high specificity, these methods influence the natural functions due to the rather large size of the proteins used. Here we present a two-step labeling procedure for the attachment of various fluorescent probes to a small peptide sequence (13 amino acids) using enzyme-mediated peptide labeling in combination with palladium-catalyzed Sonogashira cross-coupling. We identified p-iodophenyl derivatives from a small library that can be covalently attached to a lysine residue within a specific 13-amino-acid peptide sequence by Escherichia coli lipoic acid ligase A (LplA). The derivatization with p-iodophenyl subsequently served as a reactive handle for bioorthogonal transition metal-catalyzed Sonogashira cross-coupling with alkyne-functionalized fluorophores on both the peptide as well as on the protein level. Our two-step labeling strategy combines high selectivity of enzyme-mediated labeling with the chemoselectivity of palladium-catalyzed Sonogashira cross-coupling.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/bc500349h | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Precision Synthesis of Conjugated Polymer Films by Surface-Confined Stepwise Sonogashira Cross-Coupling.
Molecules
November 2024
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA.
Article Synopsis
- Thin films of poly(arylene ethynylene)-conjugated polymers can be created using a specialized method called surface-confined Sonogashira cross-coupling, which offers precise control over their structure and organization.
- These polymers boast high stability and significant electronic interactions between chains, enhancing their electronic and spectroscopic properties.
- The resulting fluorescent films are highly sensitive in chemosensing applications, effectively detecting nitroaromatic explosives in water at extremely low concentrations (sub-ppt level) due to improved exciton mobility.
Triphenylamine-Based Push-Pull Dyes for Chromogenic Detection of HSO Ion in Water: The Role of Anion in the Formation of Fluorescent Organic Nanoparticles.
J Org Chem
December 2024
Department of Chemistry, Birla Institute of Technology and Science, Pilani, Telangana 500078, India.
Optical detection of the HSO ion in pure aqueous medium is rare, owing to the very high Gibbs free energy of hydration and ambiguity to distinguish with the isostructural HPO ion. Herein, a pair of triphenylamine-based push-pull dyes with different numbers of terminal pyridine fragments, connected via an acetylenic linker, were synthesized by Sonogashira cross-coupling reaction. These two dyes displayed highly selective (LOD = 15.
View Article and Find Full Text PDFTriskelion-Shaped Hexabenzocoronenes: Synthesis and Characterization of Tris-Substituted HBC Derivatives.
Chemistry
November 2024
Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nuremberg, Organic Chemistry, Nikolaus-Fiebiger-Str. 10, 91058, Erlangen, Germany.
The synthesis of unprecedented triskelion-shaped hexa-peri-hexabenzocoronenes with C, C or D symmertry is reported. We present a new, five step synthetic access to tris-iodinated HBC derivatives carrying different solubilizing moieties (tert-butyl and mesityl), which serve as suitable building blocks for further functionalization. These molecules can undergo Sonogashira cross coupling reactions to obtain a series of seven ethynyl tris-substituted HBCs.
View Article and Find Full Text PDFSynthesis of the methyl ester of 17(/)-Me-RvD5 and relief of postoperative pain in male mice.
Org Biomol Chem
December 2024
Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O Box 1068, 0316 Oslo, Norway.
The synthesis and biological evaluation of 17(/)-Me-RvD5, an analog of the specialized pro-resolving mediators RvD5 and RvD5, are presented. The synthesis was successfully accomplished utilizing Midland Alpine borane reduction, Sonogashira cross-coupling and a one-pot hydrozirconation/iodination protocol. evaluation of RvD5, RvD5 and 17(/)-Me-RvD5 in a mouse model of fracture revealed that all three compounds inhibited postoperative pain in male mice, but not in female mice.
View Article and Find Full Text PDFSynthesis of benzo[]quinazoline-1,3(2,4)-diones.
Beilstein J Org Chem
October 2024
Universität Rostock, Institut für Chemie, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Article Synopsis
- The study describes the creation of polycyclic uracil derivatives using a combination of palladium-catalyzed cross-coupling reactions and cycloisomerization with Brønsted acids.
- This new method effectively accommodates a variety of functional groups, resulting in product yields ranging from moderate to nearly complete.
- The researchers also examined how different functional groups affect the optical properties of the final compounds using UV-vis and fluorescence spectroscopy.
Want 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!