The Shocking Revelation of (S)-Propane-1,2-diol

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beta-Galactosyl transfer from lactose to acceptor alcohols (R)-(-)-butan-2-ol, (RS)-butan-2-ol, (S)-(+)-propane-1,2-diol, (RS)-propane-1,2-diol, (S)-(+)-butane-1,3-diol, (RS)-butane-1,3-diol, propane-1,3-diol, (S)-(+)-isopropylideneglycerol (1,2-O-isopropylidene-sn-glycerol) and (RS)-isopropylideneglycerol (rac-1,2-O-isopropylideneglycerol) was studied, catalysed by the beta-galactosidase (beta-D-galactoside galactohydrolase EC 3.2.1.23) of Escherichia coli.Preference for galactosyl transfer to the R-enantiomers of chiral alcohols was observed, although selectivity was not pronounced.Higher selectivity for transfer to the primary hydroxy groups of the primary-secondary diols was observed.The results are interpreted in terms of a proposed active site model for the enzyme.

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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

Some scientific research about (S)-Propane-1,2-diol

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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.

In the meantime we’ve collected together some recent articles in this area about 4254-15-3 to whet your appetite. Happy reading! category: chiral-oxygen-ligands

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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Exchange etherification of dicarbonylcyclopentadienyl(eta2-ethyl vinyl ether)iron tetrafluoroborate (4) with optically active primary and secondary alcohols yields a mixture of diastereomeric cations.These isomers are in rapid equilibrium at room temperature.The most favorable equilibrium ratio of such diastereomers (4:1) is achieved with (+)- or (-)-menthol, and the absolute configuration of the predominant diastereomer, formed with (-)-menthol, has been determined.Optically active dicarbonylcyclopentadienyl (eta2-olefin)iron tetrafluoroborate may also be prepared from optically active epoxides.A study of the circular dichroism of these optically active complexes, together with those prepared earlier from the dioxene-iron complex (1), has been carried out and a mechanism by which asymmetry is induced at the achiral metal center is proposed.These observations provide the basis for a quadrant rule relating the sign of the Cotton effect near 450 nm and the absolute configuration of the olefin-iron complex.

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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

Extracurricular laboratory:new discovery of C4H10O2

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4-Mesyloxypyran-2-ones joined to furan by a three-carbon linker undergo intramolecular-crossed [4+4]-photocycloaddition with high or complete selectivity for the exo cycloadduct. When a C2-symmetric ketal was present on the tether adjacent to the pyranone ring, moderate levels of asymmetric induction were obtained.

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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

Why Are Children Getting Addicted To C3H8O2

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Benzyloxyketones 1a and b can be reduced by fermenting bakers’ yeast to the corresponding protected (S)-diols 2a and b in 76 and 52percent yields, respectively (90 and >95percent e.e., respectively, as (R)-(+)-MTPA esters).

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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

Properties and Exciting Facts About C3H8O2

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FucO, (S)-1,2-propanediol oxidoreductase, from Escherichia coli is involved in the anaerobic catabolic metabolism of l-fucose and l-rhamnose, catalyzing the interconversion of lactaldehyde to propanediol. The enzyme is specific for the S-enantiomers of the diol and aldehyde suggesting stereospecificity in catalysis. We have studied the enzyme kinetics of FucO with a spectrum of putative alcohol and aldehyde substrates to map the substrate specificity space. Additionally, for a more detailed analysis of the kinetic mechanism, pH dependence of catalysis, stereochemistry in hydride transfer, deuterium kinetic isotope effect of hydride transfer and effect of increasing solvent viscosity were also analyzed. The outcome of this study can be summarized as follows: FucO is highly stereospecific with the highest E-value measured to be 320 for the S-enantiomer of 1,2-propanediol. The enzyme is strictly regiospecific for oxidation of primary alcohols. The enzyme prefers short-chained (2-4 carbons) substrates and does not act on bulkier compounds such as phenyl-substituted alcohols. FucO is an ‘A-side’ dehydrogenase transferring the pro-R-hydrogen of NADH to the aldehyde substrate. The deuterium KIEs of kcat and k cat/KM were 1.9 and 4.2, respectively, illustrating that hydride transfer is partially rate limiting but also that other reaction steps contribute to rate limitation of catalysis. Combining the KIE results with the observed effects of increasing medium viscosity proposed a working model for the kinetic mechanism involving slow, rate limiting, product release and on-pathway conformational changes in the enzyme-nucleotide complexes.

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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

Archives for Chemistry Experiments of C3H8O2

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(equation presented) 2,2?,6,6?-Tetrahydroxybiphenyl undergoes a facile annulation reaction with bis(mesylate) derived from (S)-1,2-propanediol in the presence of Cs2CO3 to give the corresponding asymmetric desymmetrization product of S axial chirality with exclusive diastereoselectivity. The desymmetrization product can be utilized as a versatile chiral building block in asymmetric synthesis of axially chiral 6,6?-disubstituted 2,2?-biphenyldiols.

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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

Top Picks: new discover of 24621-61-2

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Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.

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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

Properties and Exciting Facts About (2S,3S)-Butane-2,3-diol

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The present study was undertaken to examine structural features of L- chicoric acid (3) which are important for potency against purified HIV-1 integrase and for reported cytoprotective effects in cell-based systems. Through a progressive series of analogues, it was shown that enantiomeric D- chicoric acid (4) retains inhibitory potency against purified integrase equal to its L-counterpart and further that removal of either one or both carboxylic functionalities results in essentially no loss of inhibitory potency. Additionally, while two caffeoyl moleties are required, attachment of caffeoyl groups to the central linking structure can be achieved via amide or mixed amide/ester linkages. More remarkable is the finding that blockage of the catechol functionality through conversion to tetraacetate esters results in almost no loss of potency, contingent on the presence of at least one carboxyl group on the central linker. Taken as a whole, the work has resulted in the identification of new integrase inhibitors which may be regarded as bis-caffeoyl derivatives of glycidic acid and amino acids such as serine and beta-aminoalanine. The present study also examined the reported ability of chicoric acid to exert cytoprotective effects in HIV-infected cells. It was demonstrated in target and Cell-based assays that the chicotic acids do not significantly inhibit other targets associated with HIV-1 replication, including reverse transcription, protease function, NCp7 zinc finger function, or replication of virus from latently infected cells. In CEM cells, for both the parent chicoric acid and selected analogues, antiviral activity was observable under specific assay conditions and with high dependence on the multiplicity of viral infection. However, against HIV, 1- and HIV-2-infected MT-4 cells, the chicoric acids and their tetraacetylated esters exhibited antiviral activity (50% effective concentration (EC50) ranging from 1.7 to 20 muM and 50% inhibitory concentration (IC50) ranging from 40 to 60 muM).

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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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Catalyst tune-up: A readily available, air-stable amino-sulfide catalyst, [RuCl2(PPh3){HN(C2H4SEt) 2}], has been developed. This complex displays outstanding efficiency for the hydrogenation of a broad range of substrates with C-X bonds (esters, ketones, imines), as well as for the acceptorless dehydrogenative coupling of ethanol to ethyl acetate (see scheme). Copyright

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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