Abstract
Macrolides are produced by various Streptomyces strains and make up a large group of compounds among antibiotics used against various infectious diseases. There are many criteria of classification of compounds of this type but natural macrolides usually consist of 14- or 16- membered macrocyclic lactone rings and differ from each other by the type and number of sugar moieties attached as well as by their various modes of binding to the aglycone part. Recently, renewed interest in synthesis of 16-membered macrolide derivatives has been evoked by their interesting biological properties, relatively good gastric tolerance and low tendency for producing allergy and inducing resistance. Many reviews have been devoted to the biological properties of various macrolides but only a few of them have been focused on a very important natural and semi-synthetic 16-membered macrolides and the fast growing group of their derivatives. I have, therefore, attempted to review the past and recent advances in the modifications and biological investigation of selected 16- membered leucomycin type macrolides group, including natural leucomycins (kitasamycins), spiramycins, midecamycins, semi-synthetic rokitamycin and miocamycin as well as 16-membered macrolides not belonging to the leucomycin group – tylosins and desmycosins, important from the biological application point of view. This review is dedicated to organic chemists who wish to stay abreast with the modification and properties of 16-membered macrolides and their derivatives. Despite enormous number of studies of diverse derivatives of leucomycin-type macrolides as well as tylosins and desmycosins, the 16-membered macrolides, due to their high biological potential and many possibilities for further modifications, have not yet revealed all their secrets.
Keywords: 16-membered macrolides, leucomycin, tylosin, desmycosin, antibiotics, synthesis of macrolides derivatives, biological activity, macrolide applications, Poecillastrin D, Misakinolide, Erythromycins, Oleandomycin, Sporeamicin, Spiramycins, Midecamycins, Roxithromycin, Azithromycin, Rokitamycin, Dirithromycin, Miocamycin, Flurithromycin, Clarithromycin, Davericin, Decarestrictine M, Octalactin A, Botcinolide, Amphidinolide W, Formosalide A, Tedanolide C, Amphidinolide T, Amphidinolide U, Dolabelide B, Bryostatin 10, Amphotericin B, Misakinolide A, Streptomyces kitasatoensis, Streptococcus pneumoniae, leucomycin A7, Enterococcus faecalis, Mycobacterium vaccae, Haloarcula marismortui, Staphylococcus albus, Escherichia coli, Streptomyces coelicolor, bitespiramycins, Tylosins, Streptomyces fradiae, 20-deoxo-20-morpholinotylosin, Pasteurella multocida, Pasteurella haemolytica, Haemophilus influenzae, TBDPSCl, Mitsunobu reaction, PSCB-0543, Wallach reaction
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
26