Total synthesis of antibiotics: recent achievements, limitations, and perspectives

Prusov, Evgeny V.

doi:10.1007/s00253-013-4757-5

Cited by 4 publications

(2 citation statements)

References 107 publications

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“…3-Acyltetramic acids 1 are core structural skeletons found in a wide range of natural products, exhibiting diverse biological activity. [1][2][3] Several are of interest for their antibacterial activity, notable examples being equisetin, 4 reutericyclin, 5 kibdelomycin, 6 and streptolodygin, 7 and significant progress in the development of synthetic routes to such systems 8 and their analogues has recently been made. 3 Interestingly, methodology for the general preparation of β-tricarbonyl systems is scarce, 9 and we have recently reported methodology providing access to highly substituted 3-acyltetramates, which relies upon Dieckmann cyclisation of templates 2 derived from serine, 10 threonine 11 or cysteine, 12 the chemoselectivity of which can be controlled by judicious use of reaction conditions and substituents to give products 3 and/or 4 (Scheme 1).…”

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confidence: 99%

Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity

2014

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An efficient approach for the introduction of 3-acyl side chain groups onto a core tetramate system, which are suitable for further manipulation by nucleophilic displacement or Horner-Wadsworth-Emmons coupling, provides access to a diverse library of substituted tetramates related to two distinct classes of natural products, equisetin and pramanicin. Assessment against S. aureus and E. coli indicated that some compounds exhibit significant antibacterial activity, providing unusual leads for further optimisation in the drug discovery process.

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confidence: 99%

Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity

2014

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“…Nevertheless, until such alternatives are identified, antibiotics will maintain their pivotal role. Antibiotics are presently synthesized through various methods, including fermentation [9], chemical synthesis [10,11], and enzymatic (semi-synthetic) methods [12]. The fermentation method is susceptible to the influence of various factors, impacting the quality of the process, making product separation challenging, and often resulting in lower purity.…”

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confidence: 99%

Enhanced catalytic performance of penicillin G acylase by covalent immobilization onto functionally-modified magnetic Ni0.4Cu0.5Zn0.1Fe2O4 nanoparticles

Lv,

Wang,

et al. 2024

PLoS ONE

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With the emergence of penicillin resistance, the development of novel antibiotics has become an urgent necessity. Semi-synthetic penicillin has emerged as a promising alternative to traditional penicillin. The demand for the crucial intermediate, 6-aminopicillanic acid (6-APA), is on the rise. Enzyme catalysis is the primary method employed for its production. However, due to certain limitations, the strategy of enzyme immobilization has also gained prominence. The magnetic Ni0.4Cu0.5Zn0.1Fe2O4 nanoparticles were successfully prepared by a rapid-combustion method. Sodium silicate was used to modify the surface of the Ni0.4Cu0.5Zn0.1Fe2O4 nanoparticles to obtain silica-coated nanoparticles (Ni0.4Cu0.5Zn0.1Fe2O4-SiO2). Subsequently, in order to better crosslink PGA, the nanoparticles were modified again with glutaraldehyde to obtain glutaraldehyde crosslinked Ni0.4Cu0.5Zn0.1Fe2O4-SiO2-GA nanoparticles which could immobilize the PGA. The structure of the PGA protein was analyzed by the PyMol program and the immobilization strategy was determined. The conditions of PGA immobilization were investigated, including immobilization time and PGA concentration. Finally, the enzymological properties of the immobilized and free PGA were compared. The optimum catalytic pH of immobilized and free PGA was 8.0, and the optimum catalytic temperature of immobilized PGA was 50°C, 5°C higher than that of free PGA. Immobilized PGA in a certain pH and temperature range showed better catalytic stability. Vmax and Km of immobilized PGA were 0.3727 μmol·min-1 and 0.0436 mol·L-1, and the corresponding free PGA were 0.7325 μmol·min-1 and 0.0227 mol·L-1. After five cycles, the immobilized enzyme activity was still higher than 25%.

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Pushing the Boundaries of Vinylogous Reactivity: Catalytic Enantioselective Mukaiyama Aldol Reactions of Highly Unsaturated 2‐Silyloxyindoles

Curti

Sartori

Battistini

et al. 2015

Chemistry A European J

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The first example of catalytic, enantioselective hypervinylogous Mukaiyama aldol reaction (HVMAR) involving multiply unsaturated 2-silyloxyindoles is reported. The reaction utilizes a chiral Lewis base-catalyzed Lewis acid-mediated technology to deliver homoallylic 3-polyenylidene 2-oxindoles with extraordinary levels of regio-, enantio-, and geometrical selectivity. This work highlights a subtle yet decisive influence of the indole N-substituents on the propagation of the vinylogous reactivity space of the donor substrates up to ten bonds away from the origin of the vinylogy effect. Analysis of the (13) C NMR chemical shifts of the C-ω remote site within homologous silyloxyindole donors enabled rationalization of the results and easy qualitative prediction of the HVMAR reactivity/inertia toward a given aldehyde acceptor.

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Total synthesis of antibiotics: recent achievements, limitations, and perspectives

Abstract: JournalApplied microbiology and biotechnology Introduction.

Cited by 4 publications

References 107 publications

Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity

Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity

Enhanced catalytic performance of penicillin G acylase by covalent immobilization onto functionally-modified magnetic Ni0.4Cu0.5Zn0.1Fe2O4 nanoparticles

Pushing the Boundaries of Vinylogous Reactivity: Catalytic Enantioselective Mukaiyama Aldol Reactions of Highly Unsaturated 2‐Silyloxyindoles

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