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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

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New research progress on 4254-15-3 in 2021.The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. Formula: C3H8O2, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent,Which mentioned a new discovery about 4254-15-3

(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

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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

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New research progress on 4254-15-3 in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. Computed Properties of C3H8O2, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent,Which mentioned a new discovery about 4254-15-3

The first total synthesis of Botryolide B is described from easily accessible starting materials. The synthetic strategy involves Jacobsen resolution, Sharpless epoxidation, Swern oxidation, Yamaguchi reaction, and ring closing metathesis (RCM).

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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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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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Eleven new chiral macrocycles (1-11, see Figure 1) of the pyridino-18-crown-6 type have been prepared.Nine diazapyridino-crown ligands contain two amide (1, R = benzyl; 4, R = phenyl), two N-methylamide (7, R = phenyl), two thionoamide (2, R = benzyl; 5, R = phenyl), two N-methylthionoamide (8, R = phenyl), two amine (3, R = benzyl; 6, R = phenyl), or two N-methylamine (9, R = phenyl) groups incorporated into the macroring.The appropriate chiral diamine was treated with dimethyl 2,6-pyridinedicarboxylate (or 2,6-pyridinedicarboxyl dichloride),O,O’-dimethyl 2,6-pyridinedicarbothioate, or 2,6-pyridinedimethyl ditosylate to prepare these materials.The macrocyclic diamides were also converted to the macrocyclic dithionoamides using Lawesson’s reagent and the latter macrocycles were reduced to the diamines.A new symmetrically substituted dimethylazapyridino-18-crown-6 ligand (10) and its N-acetyl derivative 11 were also prepared.The interactions of some of the new chiral ligands with (R)- and (S)-ammonium perchlorate were studied by 1H NMR spectral techniques.The degree of enantiomeric recognition was determined by the difference of the free energy of activation values (DeltaDeltaGexcit.) and the difference in log K values for these interactions.The X-ray analyses of the dithionoamido ligands (2, 5, and 8) showed severe deviations of the S and N atoms from the plane of the pyridine ring, especially in the case of 8.The optical rotations of 8 changed with time due to conformational changes.The relevant conformations of 8 are discussed in light of the X-ray crystallography, molecular mechanics, and 1H NMR spectra.

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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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The synthesis and gamma-secretase inhibition data for a series of carbamate-appended N-alkylsulfonamides are described. Carbamate 54 was found to significantly reduce brain Abeta in transgenic mice. 54 was also found to possess markedly improved brain levels in transgenic mice compared to previously disclosed 1 and 2.

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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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A dimer bearing two phenylterthiophene parts linked by a chiral moiety with a minimized molecular volume has been synthesized. This chiral dimer exhibits a chiral nematic phase and its helical structure can be fixed by cooling rapidly. The helical pitch is shorter than the visible light wavelength and the reflection band can be tuned between near ultraviolet and infrared wavelengths by mixing enantiomers of the dimer or changing the temperature. The hole and electron mobilities in the chiral nematic phase are of the order of 10-5 cm2 V-1 s-1. Circularly polarized light emission has been observed in the chiral nematic phase. In the fluidic chiral nematic phase, circularly polarized photoluminescence can be switched to a non-polarized state reversibly by the application of the electric field.

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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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The epichlorohydrin (R)-(chloromethyl)oxirane has been prepared from rac-3-chloropropane-1,2-diol by means of the chiral ketone D-camphorquinone (1,7,7-trimethylbicyclo<2.2.1>heptane-2,3-dione).These reactions lead to intermediate dioxolanes which can be converted directly into oxiranes.This conversion was effected by reduction of the C-2-ketone of the dioxolane intermediate with sodium borohydride prior to reaction with hydrogen bromide-acetic acid followed by treatment of the resulting acetoxy bromide with sodium ethane-1,2-diolate.The diastereoselective formation of other dioxolanes was also investigated by reaction of D-camphorquinone with ethane-1,2-diol, propane-1,2-diol, and 3,3-dimethylbutane-1,2-diol.

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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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From the water-soluble fraction of a methanol extract of leaves of Alangium premnifolium, two new megastigmane glycosides, alangionosides N and O, along with three known megastigmane glycosides, dendranthemoside A and alangionosides A and B, were isolated. Shimaurinosides A and B, xylopyranosyl(1?6)glucopyranosides of simple alcohols were also found to be constituents of the water-soluble fraction. Structures were determined by spectroscopic analyses.

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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