Publication
SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models
Abstract
The first examples of macrocyclization using the intramol. SNAr reaction are reported. The method has allowed the efficient prepn. of the elusive 16-membered macrocyclic COD and DOE rings related to vancomycin. The mild conditions used allow the incorporation of very racemization-prone amino acids, such as p-methoxyphenylglycine, into the peptide chain. After serving as an activator, the nitro group ortho to the diaryl ether linkage is converted either into a chlorine or a hydrogen atom, thus achieving the substitution pattern found in the vancomycin family of glycopeptides. When compd. I 20 was submitted to the same macrocyclization conditions, two atropisomers II 21 and III 22 were isolated and characterized. [on SciFinder (R)]
Official source
About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.
Related concepts (24)
Vancomycin
Vancomycin is a glycopeptide antibiotic medication used to treat a number of bacterial infections. It is used intravenously (injection into a vein) as a treatment for complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also taken orally (by mouth) as a treatment for severe Clostridium difficile colitis. When taken orally it is poorly absorbed.
Peptide synthesis
In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus).
Teicoplanin
Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis. It is a semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India).
Related publications (33)
Gas/Surface reactions probed by reflection absorption infrared spectroscopy
In my thesis, I present an investigation of the dissociation reactions of gas phase molecules on single crystal metal surfaces studied by a molecular beam in combination with Reflection Absorption Infrared Spectroscopy (RAIRS). Two gas/surface systems were ...
EPFL2023Oxidase-Type C-H/C-H Coupling Using an Isoquinoline-Derived Organic Photocatalyst
Oxidase-type oxidation is an attractive strategy in organic synthesis due to the use of O-2 as the terminal oxidant. Organic photocatalysis can effect metal-free oxidase chemistry. Nevertheless, current methods are limited in reaction scope, possibly due t ...
WILEY-V C H VERLAG GMBH2022Competitive Dehydrogenation and Backbone Fragmentation of Superhydrogenated PAHs: A Laboratory Study
Eduardo Carrascosa Casado, Robert Richter
Superhydrogenated polycyclic aromatic hydrocarbons (PAHs) have been suggested to catalyze the formation of H-2 in certain regions of space, but it remains unclear under which circumstances this mechanism is viable given the reduced carbon backbone stabilit ...
2021