- Synthesis of (S)-3-hydroxytetrahydropyran from L-glutamic acid
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A concise synthesis of (S)-3-hydroxytetrahydropyran from natural L-glutamic acid has been developed. The intramolecular etherification starting from 1,5-diol was promoted by trifluoromethanesulfonic anhydride. The clinnamates of the alcohols were prepared
- Geng, Yang,Zheng, Maolin,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
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- Synthesis of Two Epimers of Pseudopaline
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Opines are a known group of compounds characterized by an elevated polarity. Recently, two new members of this class, staphylopine and pseudopaline, have been identified in Staphylococcus aureus and Pseudomonas aeruginosa, respectively. These molecules are metal chelators that contribute to the growth of bacteria in particularly metal-poor environment. Different evidences suggest that these molecules might have an important role in the development of pulmonary infections in humans. Considering the impact of P. aeruginosa infections in cystic fibrosis patients (prevalence up to 70 percent), pseudopaline has risen interest as potential source of new therapeutic intervention. We present herein a straightforward synthetic approach for the synthesis of the two epimers of pseudopaline. Starting from a chiral building block, we attribute the absolute configuration to the two obtained diasteroisomers.
- Arnoux, Pascal,Cavelier, Florine,Cullia, Gregorio,Fanelli, Roberto,Voulhoux, Romé
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supporting information
(2020/07/06)
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- GADOLINIUM BEARING PCTA-BASED CONTRAST AGENTS
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The present invention relates to the RRR/SSS pair of enantiomers of the of Gd(PCTA-tris-glutamic acid), the single enantiomers of the pair, the pharmaceutically acceptable salts thereof, their amide derivatives, and compositions comprising at least 50% of these compounds.
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Page/Page column 33
(2020/03/02)
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- Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds
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To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral α-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90percent) and good enantioselectivities (60-74percent). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.
- Riatto, Valéria B.,Victor, Mauricio M.,Sousa, Jaqueline F.,Menegola, Carla
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p. 149 - 157
(2018/12/13)
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- 3-benzyloxy-tetrahydropyrane, preparation method thereof and preparation method of single-configured tetrahydropyrane-3-cyclitol
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The invention relates to 3-benzyloxy-tetrahydropyrane, a preparation method thereof and a preparation method of single-configured tetrahydropyrane-3-cyclitol, and belongs to the technical field of medicines. The 3-benzyloxy-tetrahydropyrane has a structur
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Paragraph 0046; 0047; 0048; 0049
(2017/10/27)
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- COMPOSITIONS FOR THE TREATMENT OF INFLAMMATORY DISEASES
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This invention provides compounds, methods and compositions for the treatment of inflammatory diseases, comprising the timely administration of a provided compound, which has a structure related to an endogenously formed lipid mediator. One embodiment of the present invention is directed to a compound selected from a group having the general formula A.
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Page/Page column 9; 48; 49
(2014/09/03)
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- Stereocontrolled total synthesis of the potent anti-inflammatory and pro-resolving lipid mediator resolvin D3 and its aspirin-triggered 17 R-epimer
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The first total synthesis of stereochemically pure resolvin D3 and aspirin-triggered resolvin D3 is reported. These enzymatic metabolites of docosahexaenoic acid (DHA) have potent anti-inflammatory and pro-resolving actions. The convergent synthetic strategy is based on enantiomerically pure starting materials, and it is highly stereocontrolled.
- Winkler, Jeremy W.,Uddin, Jasim,Serhan, Charles N.,Petasis, Nicos A.
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supporting information
p. 1424 - 1427
(2013/06/27)
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- Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine
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A study into the synthesis and synthetic utility of (S)-3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide is described. This nitrone is readily accessed from l-glutamic acid and the regio- and stereoselectivity of cycloaddition of this compound with a range
- Ashoorzadeh, Amir,Archibald, Glenn,Caprio, Vittorio
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experimental part
p. 4671 - 4680
(2009/10/09)
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- Phase-transfer catalyzed glycolate conjugate addition
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Cinchonine based phase-transfer catalysts were developed for enantioselective conjugate additions to electron deficient alkenes, including acylates, acrylonitrile, and chalcone. N-Trifulorobenzyl cinchoninium bromide 6 catalyst (20 mol %) in THF at -40 °C promoted the conjugate addition of arylketone glycolate 1 generating S-product 2 in good yields and selectivities. Catalyst, solvent, and base variations are presented along with conditions to convert the products to intermediates useful for multistep applications.
- Andrus, Merritt B.,Ye, Zhifeng
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p. 534 - 537
(2008/04/13)
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- A convergent enantioselective synthesis of the anti-malarial agent (+)-febrifugine
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Chiral pool derived 3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide underwent regio- and diastereoselective 1,3-dipolar cycloaddition with N-allylquinazolone to give a cycloadduct that was elaborated to (+)-febrifugine a potent anti-malarial alkaloid.
- Ashoorzadeh, Amir,Caprio, Vittorio
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p. 346 - 348
(2007/10/03)
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- Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid
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An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells.
- Rustoy, Eduardo M.,Pereyra, Elba N.,Moreno, Silvia,Baldessari, Alicia
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p. 3763 - 3768
(2007/10/03)
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- Transfer hydrogenation of activated ketones using novel chiral Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes
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A series of α-keto esters and α,α,α- trifluoromethyl ketones were reduced in high yields and excellent enantioselectivities under Ru-catalysed transfer hydrogenation using novel chiral N-arenesulfonyl-1,2-diphenylethylenediamine ligands.
- ?terk, Damjan,Stephan, Massoud S.,Mohar, Barbara
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p. 535 - 537
(2007/10/03)
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- Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
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Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.
- Drioli, Sara,Nitti, Patrizia,Pitacco, Giuliana,Tossut, Laura,Valentin, Ennio
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p. 2713 - 2728
(2007/10/03)
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- Stereospecific ketonization of 2-hydroxymuconate by 4-oxalocrotonate tautomerase and 5-(carboxymethyl)-2-hydroxymuconate isomerase
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4-Oxalocrotonate tautomerase from Pseudomonas putida mt-2 and 5-(carboxymethyl)-2-hydroxymuconate isomerase from Escherichia coli C catalyze the same reaction on substrates that differ only by a carboxymethyl group. While the structural resemblances betwe
- Whitman, Christian P.,Hajipour, Gholamhossein,Watson, Robert J.,Johnson Jr., William H.,Bembenek, Michael H.,Stolowich, Neal J.
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p. 10104 - 10110
(2007/10/02)
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- Stereochemical Studies on Porphyrin a: Assignment of the Absolute Configuration of a Model Porphyrin by Degradation
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The synthesis is described of a porphyrin alcohol (22) which has a structure very similar to that of porphyrin a (2).The model porphyrin was resolved by separation of its camphanate esters.Ozonolysis of the 2-nitrobenzoate of each enantiomer in tritiated form gave a derivative of 2-hydroxypentadioic acid whose configuration was determined by dilution analysis.It is demonstrated that correlation of the stereochemistry of porphyrin a with that of the model (22) will be possible by means of the (1)H and (19)F n.m.r. spectra of the corresponding esters with (-)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid.
- Battersby, Alan R.,Cardwell, Kevin S.,Leeper, Finian J.
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p. 1565 - 1580
(2007/10/02)
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- NAD(P)+-NAD(P)H Models. 59. 1,2- Versus 1,4-Reduction of β,γ-Unsaturated α-Keto Ester
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Depending on the reactivity of the reducing agent, β,γ-unsaturated α-keto ester is reduced into either β,γ-unsaturated α-hydroxy ester or saturated α-keto ester as the result of 1,2- or 1,4-reduction.
- Ohno, Atsuyoshi,Yasuma, Tsuneo,Nakamura, Kaoru,Oka, Shinzaburo
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p. 2905 - 2906
(2007/10/02)
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