36061-01-5Relevant articles and documents
Versatile Ru-Photoredox-Catalyzed Functionalization of Dehydro-Amino Acids and Peptides
Brandhofer, Tobias,Manche?o, Olga García
, p. 3797 - 3801 (2019)
A versatile photoredox-catalyzed synthesis of unnatural amino acids and peptides is presented. Commercially available Ru(bpy)3(PF6)2 was efficiently used as visible light photocatalyst in combination with a broad number of
A Water-Soluble Iridium Photocatalyst for Chemical Modification of Dehydroalanines in Peptides and Proteins
van Lier, Roos C. W.,de Bruijn, A. Dowine,Roelfes, Gerard
supporting information, p. 1430 - 1437 (2020/12/11)
Dehydroalanine (Dha) residues are attractive noncanonical amino acids that occur naturally in ribosomally synthesised and post-translationally modified peptides (RiPPs). Dha residues are attractive targets for selective late-stage modification of these complex biomolecules. In this work, we show the selective photocatalytic modification of dehydroalanine residues in the antimicrobial peptide nisin and in the proteins small ubiquitin-like modifier (SUMO) and superfolder green fluorescent protein (sfGFP). For this purpose, a new water-soluble iridium(III) photoredox catalyst was used. The design and synthesis of this new photocatalyst, [Ir(dF(CF3)ppy)2(dNMe3bpy)]Cl3, is presented. In contrast to commonly used iridium photocatalysts, this complex is highly water soluble and allows peptides and proteins to be modified in water and aqueous solvents under physiologically relevant conditions, with short reaction times and with low reagent and catalyst loadings. This work suggests that photoredox catalysis using this newly designed catalyst is a promising strategy to modify dehydroalanine-containing natural products and thus could have great potential for novel bioconjugation strategies.
Dimethoxyethane as an alternative solvent for Schmidt reactions. Preparation of homochiral N-(5-oxazolyl)oxazolidinones from N-acetoacetyl derivatives of oxazolidinones
Galvez, Nicanor,Moreno-Manas, Marcial,Sebastian, Rosa M.,Vallribera, Adelina
, p. 1609 - 1616 (2007/10/03)
Dimethoxyethane is an useful solvent for the Schmidt reaction of ketones and β-ketoesters with sodium azide and methanesulfonic acid to afford amides and amidoesters. This solvent is an alternative to the unsafe chlorinated solvents normally used. A β-diketone and several (4S)-N-(2-alkylacetoacetyl)-4-benzyloxazolidin-2-ones afford oxazoles under those conditions.
