Extracurricular laboratory:new discovery of (S)-Propane-1,2-diol

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Preparation of Chiral 1,2-Alkanediols with Baker’s Yeast-Mediated Oxidation

(S)-1,2-Alkanediols, which were the opposite configuration to those produced by baker’s yeast-mediated bioreduction of corresponding 1-hydroxy-2-alkanones, were prepared by baker’s yeast-mediated oxidation.Treatment of racemic 1,2-alkanediols with baker’s yeast under the aerobic condition followed by removal of the corresponding 1-hydroxy-2-alkanones, which were produced by enantioselective oxidation of (R)-1,2-alkanediols, afforded (S)-1,2-alkanediols.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Treatment of neurodegenerative diseases

Disclosed are methods for increasing the differentiation of mammalian neuronal cells for purposes of treating neurodegenerative diseases or nerve damage by administration of various compounds including alcohols, diols and/or triols and their analogues.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

More research is needed about C3H8O2

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Optical resolution, absolute configuration, and activity of the enantiomers of proxyphylline

The enantiomers of proxyphylline have been separated via their corresponding camphanates. Synthesis of (+)-proxyphylline from theophylline and (S)-propylene oxide derived from (S)-lactic acid established the absolute configuration of the (+) and (-) isomer as S and R, respectively. The activity of the enantiomers as cyclic nucleotide phosphodiesterase inhibitors was tested in human lung tissue homogenate. No differences were found either between the two enantiomers or between the enantiomers and racemic proxyphylline.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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PHARMACEUTICAL FORMULATION CONTAINING AN SGLT2 INHIBITOR

Pharmaceutical formulations are provided which are in the form of capsules or tablets for oral use and which include a medicament dapagliflozin or its propylene glycol hydrate and a pharmaceutical acceptable carrier therefor, which formulation is designed for immediate release.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach

Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen’s hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Immobilized Aspergillus niger epoxide hydrolases: Cost-effective biocatalysts for the prepation of enantiopure styrene oxide, propylene oxide and epichlorohydrin

This study aimed to prepare robust immobilized epoxide hydrolase (EH) preparations for asymmetric hydrolysis of racemic epoxides such as styrene oxide, propylene oxide and epichlorohydrin. For this purpose, Aspergillus niger EH was immobilized onto Lewatit VP OC 1600 support by adsorption, modified Florisil and Eupergit C supports by covalently. The suitability of the supports was examined for protein binding capacity and rate of racemic styrene oxide hydrolysis. The protein-activity recovery yields were 75-85%, 82-78% and 90-75%, respectively for EH immobilized onto Lewatit VP OC 1600, modified Florisil and Eupergit C supports. All A. niger EH preparations catalyzed preferentially hydrolysis of (R)-epoxides. Although enantiomeric excess values of all the tested epoxides were 99%, the highest enantiopure epoxide yields were obtained as 48% for (S)-styrene oxide by the immobilized EHs onto modified Florisil and Eupergit C. The highest diol yield was obtained as 78% for 3-chloro-1,2-propanediol, however, its enantiomeric excess value was 28.2%. Enantioselectivity of A. niger EH was improved with the preparation of mentioned immobilized forms. The highest enantioselectivity value was obtained as 95 toward styrene oxide by A. niger EH immobilized onto modified Florisil . The results of reusability studies show that the immobilized EH preparations offer feasible potentials for the preparation of enantiopure epoxides than that of free form.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Asymmetric ring-opening of epoxides on chiral Co(Salen) catalyst synthesized in SBA-16 through the “ship in a bottle” strategy

Chiral Co(Salen) complex was synthesized in the mesoporous cage of SBA-16 through the “ship in a bottle” method. The pore entrance size of SBA-16 was precisely tailored by varying the autoclaving time and silylation with phenyltrimethoxysilane to trap Co(Salen) complex in the cage of SBA-16. Chiral Co(Salen) trapped in SBA-16 shows enantioselectivity (up to 87-96% ee) as high as that of the homogeneous catalyst for the asymmetric ring opening of terminal epoxides and can be recycled at least 10 times with no apparent loss of activity. The activity for the catalyst trapped inside SBA-16 can be significantly increased when the surface is modified with organic groups. This work extends the “ship in a bottle” synthesis from microporous materials to mesoporous cage-like materials and develops an effective strategy to trap metal complex catalyst with large molecular size into the nanopores or cavities of mesoporous materials.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

New explortion of (S)-Propane-1,2-diol

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Catalytic Hydrogenation of Chiral alpha-Amino and alpha-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

The hydrogenation of carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various alpha-amino and alpha-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields of the desired amino alcohols and diols were obtained without racemization. The most suitable alpha-substituents were NH2, NHR, and OH, whereas beta-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was found for alpha-NR2, alpha-OR, and unfunctionalized esters; acids and amides were also not reduced under these conditions. A working hypothesis for the mode of action of the catalyst is presented.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Enantioselective oxidation of diols by secondary alcohol dehydrogenase from Geotrichum sp. WF9101

Geotrichum sp. WF9101 could degrade (S)-(+)-1,2-propanediol, (S)-(+)- 1,3-butanediol, and (2S,4S)-(+)-2,4-pentanediol, but not the corresponding enantiomers. An NAD+-linked secondary alcohol dehydrogenase purified from the strain showed the same enantioselective oxidations towards these diols. This enzyme is proposed to be useful for the preparation of (R)-(-)-diols from the racemates of these diols.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Complexation of hydrophosphoranes: Possible mechanism and coordination activity

Complexation of (4S,9S)-4,9-diethyl-2,11-dioxa-5,8-diaza-1lambda 5-phosphatricyclo[6.3.0.01.5]undecane (1) and 3,3,8,8-tetramethyl-1,6-dioxa-4,9-diaza-5lambda 5-phosphaspiro[4,4]nonane (2) with [Rh(CO)2Cl]2; 2,3,7,8-dibenzo-1,6-dioxa-4,9-diaza-5lambda 5-phosphaspiro-[4,4]nonane (3) with [Rh(CO)2Cl]2 and [MCl2(COD)] (M = Pd, Pt); (2S,7S)-2,7-dimethyl-1,4,6,9-tetraoxa-5lambda 5-phosphaspiro[4,4]nonane (4) with [Rh(CO)2Cl]2 and [PdCl2(COD)] has been studied. The products have been characterized by 1H-, 2H-, 13C-, 31P-NMR, IR spectroscopy, laser desorption mass spectrometry and X-ray photoelectron spectroscopy. A possible mechanism for hydrophosphoranes complexation is discussed. A correlation between Lewis basicity and coordination activity has been found for ligands 1-3. Phosphorane 4 was shown to coordinate by means of the P(III)-tautomer.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate