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Enzymatic Generation of Thioaldehyde Motifs by Flavin-Dependent Cysteine Decarboxylases for Peptide Bioconjugation and Macrocyclization.
Org Lett
August 2023
State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center of Nanjing University, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Thioaldehyde is a highly electrophilic group under aqueous conditions and can be generated via oxidative enzymatic modifications of cysteine residues in peptides and proteins. Herein, we report the installation of thioaldehyde and aldehyde groups at the C-terminus of peptides by flavin-dependent cysteine decarboxylases from the biosynthesis of ribosomally synthesized and post-translationally modified peptides. The generated (thio)aldehyde is utilized as a reactive handle for peptide bioconjugation and macrocyclization.
View Article and Find Full Text PDFVisible-Light-Induced Passerini Multicomponent Polymerization.
Angew Chem Int Ed Engl
April 2019
School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, QLD, 4000, Brisbane, Australia.
Herein, we introduce an additive-free visible-light-induced Passerini multicomponent polymerization (MCP) for the generation of high molar mass chains. In place of classical aldehydes (or ketones), highly reactive, in situ photogenerated thioaldehydes are exploited along with isocyanides and carboxylic acids. Prone to side reactions, the thioaldehyde moieties create a complex reaction environment which can be tamed by optimizing the synthetic conditions utilizing stochastic reaction path analysis, highlighting the potential of semi-batch procedures.
View Article and Find Full Text PDFEnzyme That Makes You Cry-Crystal Structure of Lachrymatory Factor Synthase from Allium cepa.
ACS Chem Biol
September 2017
Department of Pharmacology, School of Medicine, Case Western Reserve University, Cleveland, Ohio, United States.
The biochemical pathway that gives onions their savor is part of the chemical warfare against microbes and animals. This defense mechanism involves formation of a volatile lachrymatory factor (LF) ((Z)-propanethial S-oxide) that causes familiar eye irritation associated with onion chopping. LF is produced in a reaction catalyzed by lachrymatory factor synthase (LFS).
View Article and Find Full Text PDFStepwise Light-Induced Dual Compaction of Single-Chain Nanoparticles.
Macromol Rapid Commun
August 2017
Macromolecular Architectures, Institute for Chemical Technology and Polymer Chemistry, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76131, Karlsruhe, Germany.
A photochemical strategy for the sequential dual compaction of single polymer chains is introduced. Two photoreactive methacrylates, with side chains bearing either a phenacyl sulfide (PS) or an α-methylbenzaldehyde (photoenol, PE) moiety, are selectively incorporated by one-pot iterative reversible-addition fragmentation chain transfer copolymerization into the outer blocks of a well-defined poly(methyl methacrylate) based ABC triblock copolymer possessing a nonfunctional spacer block (M = 23 400 g mol , Đ = 1.2; ≈15 units of each photoreactive moieties of each type) as well as in model statistical copolymers bearing only one type of photoreactive unit.
View Article and Find Full Text PDFCleaving Direct-Laser-Written Microstructures on Demand.
Angew Chem Int Ed Engl
May 2017
Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76131, Karlsruhe, Germany.
Using an advanced functional photoresist we introduce direct-laser-written (DLW) 3D microstructures capable of complete degradation on demand. The networks consist exclusively of reversible bonds, formed by irradiation of a phenacyl sulfide linker, giving disulfide bonds in a radical-free step-growth polymerization via a reactive thioaldehyde. The bond formation was verified in solution by ESI-MS.
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