Total Synthesis of the Trisaccharide Antigen of theCampylobacter jejuniRM1221 Capsular Polysaccharide via de Novo Synthesis of the 6-Deoxy-d-manno-heptose Building Blocks

2019 ◽  
Vol 84 (5) ◽  
pp. 2393-2403 ◽  
Author(s):  
Xiaoman Wang ◽  
Yan Chen ◽  
Junchang Wang ◽  
You Yang
Keyword(s):  
Total Synthesis ◽  
Capsular Polysaccharide ◽  
De Novo ◽  
Building Blocks ◽  
De Novo Synthesis

De Novo Synthesis of l-Colitose and l-Rhodinose Building Blocks

2011 ◽  
Vol 77 (2) ◽  
pp. 870-877 ◽  
Author(s):  
Oliviana Calin ◽  
Rajan Pragani ◽  
Peter H. Seeberger
Keyword(s):  
De Novo ◽  
Building Blocks ◽  
De Novo Synthesis

A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-ester Acceptors Using a Desaturative Amination–Cyclization Approach

Synthesis ◽  
2021 ◽  
Author(s):  
Henry P. Caldora ◽  
Sebastian Govaerts ◽  
Shashikant U. Dighe ◽  
Oliver J. Turner ◽  
Daniele Leonori
Keyword(s):  
Amino Acids ◽  
Primary Amine ◽  
De Novo ◽  
Building Blocks ◽  
De Novo Synthesis ◽  
Keto Ester ◽  
Mild Conditions ◽  
Blockbuster Drug

Here we report a desaturative approach for oxindole synthesis. This method uses simple γ-ester-containing cyclohexanones and primary amine building blocks as coupling partners. A dual photoredox–cobalt manifold is used to generate a secondary aniline that, upon heating, cyclizes with the pendent ester functionality. The process operates under mild conditions and was applied to the modification of several amino acids, the blockbuster drug mexiletine, as well as the formation of dihydroquinolinones.

scholarly journals De novo synthesis, structural assignment and biological evaluation of pseudopaline, a metallophore produced by Pseudomonas aeruginosa

2019 ◽  
Vol 10 (27) ◽  
pp. 6635-6641 ◽  
Author(s):  
Jian Zhang ◽  
Tianhu Zhao ◽  
Rongwen Yang ◽  
Ittipon Siridechakorn ◽  
Sanshan Wang ◽  
...  
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Total Synthesis ◽  
Natural Product ◽  
Absolute Configuration ◽  
De Novo ◽  
Biological Evaluation ◽  
De Novo Synthesis ◽  
Structural Assignment ◽  
The Absolute

The first total synthesis and isolation of pseudopaline was reported, which allows determination and confirmation of the absolute configuration of the natural product.

scholarly journals Total synthesis of aStreptococcus pneumoniaeserotype 12F CPS repeating unit hexasaccharide

2017 ◽  
Vol 13 ◽  
pp. 164-173 ◽  
Author(s):  
Peter H Seeberger ◽  
Claney L Pereira ◽  
Subramanian Govindan
Keyword(s):  
Total Synthesis ◽  
Capsular Polysaccharide ◽  
Severe Disease ◽  
Building Blocks ◽  
Positive Bacterium ◽  
Linear Approach ◽  
Starting Point ◽  
Branching Points ◽  
Glycoconjugate Vaccines ◽  
Sequential Assembly

The Gram-positive bacteriumStreptococcus pneumoniaecauses severe disease globally. Vaccines that preventS. pneumoniaeinfections induce antibodies against epitopes within the bacterial capsular polysaccharide (CPS). A better immunological understanding of the epitopes that protect from bacterial infection requires defined oligosaccharides obtained by total synthesis. The key to the synthesis of theS. pneumoniaeserotype 12F CPS hexasaccharide repeating unit that is not contained in currently used glycoconjugate vaccines is the assembly of the trisaccharide β-D-GalpNAc-(1→4)-[α-D-Glcp-(1→3)]-β-D-ManpNAcA, in which the branching points are equipped with orthogonal protecting groups. A linear approach relying on the sequential assembly of monosaccharide building blocks proved superior to a convergent [3 + 3] strategy that was not successful due to steric constraints. The synthetic hexasaccharide is the starting point for further immunological investigations.

scholarly journals Kā raugs uzvedas, kad tam atņem būvelementus?

2021 ◽  
Author(s):  
Ernests Tomass Auziņš ◽  
Keyword(s):  
Ethanol Production ◽  
Building Block ◽  
De Novo ◽  
Building Blocks ◽  
Central Metabolism ◽  
De Novo Synthesis ◽  
Brewer’S Yeast ◽  
Glycerol Production ◽  
Brewer's Yeast ◽  
Insight Into

The study explored changes in carbon fluxes in the central metabolism of brewer’s yeast in the absence of building blocks such as adenine or nitrogen. These flows provide insight into changes in the central metabolism of brewer’s yeast. It was found that in the absence of a building block, the yeast mainly uses fermentation for growth, producing ethanol. Deletion of Δade1 in purine de novo synthesis reduces ethanol production, and decreased glycerol production in adenine starvation indicates a slowing of central metabolism.

scholarly journals Strategies for the De Novo Synthesis of Highly Substituted Pyridine Scaffolds: Unified Total Synthesis of the Limonoid Alkaloids

2021 ◽  
Author(s):  
Timothy Newhouse ◽  
Alexander Schuppe ◽  
Yannan Liu ◽  
Yizhou Zhao ◽  
Sebastian Ibarran ◽  
...  
Keyword(s):  
Total Synthesis ◽  
De Novo ◽  
Biologically Active ◽  
Synthetic Analog ◽  
De Novo Synthesis ◽  
Xylocarpus Granatum ◽  
Benzylic Oxidation ◽  
Substituted Pyridines ◽  
Active Natural ◽  
Core Framework

Highly substituted pyridine scaffolds are found in many biologically active natural products and therapeutics. Accordingly, numerous complementary de novo approaches to obtain differentially substituted pyridines have been disclosed. This article delineates the evolution of the synthetic strategies designed to assemble the demanding tetrasubstituted pyridine core present in the limonoid alkaloids isolated from Xylocarpus granatum, including xylogranatopyridine B, granatumine A and related congeners. The most efficient and convergent construction of the core framework present in xylogranatopyridine B involved a Liebeskind pyridine synthesis and late-stage benzylic oxidation. By contrast, the synthesis of the bislactone limonoid alkaloids, such as granatumine A which exhibited moderate PTP1B-inhibitory activities, necessitated the development of a novel pyran-to-pyridine conversion. In addition, NMR calculations suggested structural misassignment of several limonoid alkaloids, and predicted their C3-epimers as the correct structures, which was further validated unequivocally through chemical synthesis. While preliminary results of the pNPP assays showed that these bislactone limonoid alkaloids were only weakly inhibitory against PTP1B, C3-deoxy-xylogranatin F, an unnatural synthetic analog, was demonstrated to be more potent than the other congeners.

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