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13C NMR, alone or in combination with 1H NMR, allows the assignment of the absolute configuration of chiral alcohols, amines, carboxylic acids, thiols, cyanohydrins, sec,sec-diols and sec,sec-aminoalcohols, derivatized with appropriate chiral auxiliaries. This extends the assignment possibilities of NMR to fully deuterated and to nonproton containing compounds.

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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 gene encoding a putative (R,R)-butane-2,3-diol dehydrogenase (bdhA) from Bacillus clausii DSM 8716T was isolated, sequenced and expressed in Escherichia coli. The amino acid sequence of the encoded protein is only distantly related to previously studied enzymes (identity 33?43%) and exhibited some uncharted peculiarities. An N-terminally StrepII-tagged enzyme variant was purified and initially characterized. The isolated enzyme catalyzed the (R)-specific oxidation of (R,R)- and meso-butane-2,3-diol to (R)- and (S)-acetoin with specific activities of 12 U/mg and 23 U/mg, respectively. Likewise, racemic acetoin was reduced with a specific activity of up to 115 U/mg yielding a mixture of (R,R)- and meso-butane-2,3-diol, while the enzyme reduced butane-2,3-dione (Vmax 74 U/mg) solely to (R,R)-butane-2,3-diol via (R)-acetoin. For these reactions only activity with the co-substrates NADH/NAD+ was observed. The enzyme accepted a selection of vicinal diketones, alpha-hydroxy ketones and vicinal diols as alternative substrates. Although the physiological function of the enzyme in B. clausii remains elusive, the data presented herein clearly demonstrates that the encoded enzyme is a genuine (R,R)-butane-2,3-diol dehydrogenase with potential for applications in biocatalysis and sensor development.

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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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White biotechnology relies on the sophisticated chemical machinery inside living cells for producing a broad range of useful compounds in a sustainable and environmentally friendly way. However, despite the impressive repertoire of compounds that can be generated using white biotechnology, this approach cannot currently fully replace traditional chemical production, often relying on petroleum as a raw material. One challenge is the limited number of chemical transformations taking place in living organisms. Biocompatible chemistry, that is non-enzymatic chemical reactions taking place under mild conditions compatible with living organisms, could provide a solution. Biocompatible chemistry is not a novel invention, and has since long been used by living organisms. Examples include Fenton chemistry, used by microorganisms for degrading plant materials, and manganese or ketoacids dependent chemistry used for detoxifying reactive oxygen species. However, harnessing biocompatible chemistry for expanding the chemical repertoire of living cells is a relatively novel approach within white biotechnology, and it could potentially be used for producing valuable compounds which living organisms otherwise are not able to generate. In this mini review, we discuss such applications of biocompatible chemistry, and clarify the potential that lies in using biocompatible chemistry in conjunction with metabolically engineered cell factories for cheap substrate utilization, improved cell physiology, efficient pathway construction and novel chemicals production.

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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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Intramolecular Pauson-Khand reactions of 1,6-enynes 3a-c with a methylenecyclopropane terminator and a chiral acetal moiety adjacent to the triple bond gave spiro 5a-c in good yields with a diastereoselectivity of up to 6.4:1.The major diastereomer of 5b was converted to enantiomerically pure bicyclo<3.3.0>octane-3,8-dione 8, which showed a negative peak at 287 nm in the CD curve, consistent with an assumed (5R) configuration.Keywords: Pauson-Khand reaction, intramolecular; methylenecyclopropanes, double bond activation in; spirooct-1-en-3-ones>; enentiomerically pure compounds; stereoselection.

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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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Lipase from Pseudomonas capacia (PCL, Amano PS) catalyzed the enantioselective diacetylation of (+/-)-2,3-butanediol in vinyl acetate.Both acetylation steps favored the (R)-enantiomer (E1 = 12, E2 = 34), thus the reaction is a sequential kinetic resolution.The enantioselectivities of the two steps reinforced one another because both steps proceeded at comparable rates (S = 3) yielding an overall enantioselectivity of approximately 200.A synthetic-scale resolution starting from 2.7 g of (+/-)-2,3-butanediol yielded the diacetate ester of (R)-(-)-butanediol with 96percent ee (1.6 g, 30percent yield) and (S)-(+)-butanediol with 99percent ee (0.63 g, 23percentyield).This preparation is carried out entirely in organic solvent, thereby avoiding the difficult and low yield extraction of 2,3-butanediol from aqueous solution.

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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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Three commercial yeasts strains, namely, Saccharomyces cerevisiae SY, DV10, and Drop Acid Yeast, were used for Dangshan pear wine fermentation. Monitoring main physical and chemical indexes and scoring comprehensive sensory characteristics to find a suitable yeast to produce Dangshan pear wine. The fermentation cycle of SY was short (15 days), and the SY-fermented wine had a suitable sugar-acid ratio, with a residual sugar content of 3.13 ± 0.05 g/L, total acid content of 3.40 ± 0.11 g/L, and ethanol content of 14.1 ± 0.27% (v/v). Additionally, 42 flavor compounds were detected in fermented Dangshan pear wine, and the total amount of flavor compounds was highest in the SY wine (2,584.72 mug/L). Combined with the comprehensive sensory evaluation scores, these results suggest that Saccharomyces cerevisiae SY was the most suitable strain to produce Dangshan pear wine. Practical applications: In this study, we compared the physical and chemical indicators of pear wine brewed by different Saccharomyces cerevisiae in the process of fermentation and the final quality of pear wine products. It was concluded that the pear wine produced by Saccharomyces cerevisiae SY had good quality. The study found a strain suitable for the fermentation of pear wine and provided a theoretical basis for the industrial production of pear wine. Next, we can try to use Saccharomyces cerevisiae SY for large-scale production of pear wine and try to sell it on the market.

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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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An enzyme capable of reducing acetoin in the presence of NADH was purified from Mycobacterium sp. B-009, a non-clinical bacterial strain of soil origin. The enzyme is a homotetramer and can be classified as a medium-chain alcohol dehydrogenase/ reductase based on the molecular weight of the monomer. Identification of the structural gene revealed a limited distribution of homologous genes only among actinomycetes. In addition to its activity as a reductase specific for (S)-acetoin (EC 1.1.1.76), the enzyme showed both diacetyl reductase (EC 1.1.1.304) and NAD+ -dependent alcohol dehydrogenase (EC 1.1.1.1) activities. (S)-Acetoin and diacetyl reductases belong to a group of short-chain alcohol dehydrogenase/reductases but do not have superior abilities to dehydrogenate monoalcohols. Thus, the purified enzyme can be readily distinguished from other enzymes. We used the dual functionality of the enzyme to effectively reduce diacetyl to (S)-acetoin, coupled with the oxidation of 1-butanol.

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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 compound represented by the formula I STR1 wherein X is independently both F or both Cl or one X is independently F and the other is independently Cl; R1 is a straight or branched chain (C3 to C8) alkyl group substituted by one or two groups convertible in vivo into hydroxy moieties, (e.g., a polyether ester, amino acid ester or phosphate ester) thereof or a pharmaceutically acceptable salt thereof and pharmaceutical compositions thereof useful for treating and/or preventing fungal infections are disclosed.

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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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This study investigated the effect of raw material, pressing, and glycosidase on the aromatic profile of goji berry wine. The free-run and the pressed juice of dried and fresh goji berries were used for wine production, whereas glycosidase was applied to wine after fermentation. Dried goji berry fermented wine exhibited much stronger fruity, floral, caramel, and herbaceous odors due to higher levels of esters, beta-ionone and methionol. However, fresh berry fermented wine possessed stronger chemical notes due to higher levels of 4-ethylphenol. Pressing treatment reduced the fruity and caramel odors in these fermented wines, and fresh berry free-run juice fermented wine exhibited the least floral aroma. Glycosidase addition did not alter the aromatic composition of wines. The principal component analysis indicated that goji raw material played a primary role in differentiating the aromatic profiles of the wines due to the difference on the content of 20 esters, nine benzenes, eight aldehydes/ketones, three acids, two alcohols and six other volatiles. The content differences on isopentyl alcohol, styrene, benzyl alcohol, 1-octanol, (E)-5-decen-1-ol, 1-hexanol, and -cyclocitral resulted in the segregation of the wines with and without the pressing treatment, especially for fresh berry fermented win.

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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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N,N’-dimethyl-4,4′-azopyridinium methyl sulfate (MAZP) was characterized as an electron transfer mediator for oxidation reactions catalyzed by NAD+- and pyrroloquinoline quinone (PQQ)-dependent alcohol dehydrogenases. The bimolecular rate constant of NADH reactivity with MAZP was defined as (2.2 ± 0.1) × 105 M?1 s?1, whereas the bimolecular rate constant of reactivity of the reduced form of PQQ-dependent alcohol dehydrogenase with MAZP was determined to be (4.7 ± 0.1) × 104 M?1 s?1. The use of MAZP for the regeneration of the cofactors was investigated by applying the electrochemical oxidation of the mediator. The total turnover numbers of mediator MAZP and cofactor NADH for ethanol oxidation catalyzed by NAD+-dependent alcohol dehydrogenase depended on the concentration of the substrate and the duration of the electrolysis, and the yield of the reaction was limited by the enzyme inactivation and the electrochemical process. The PQQ-dependent alcohol dehydrogenase was more stable, and the turnover number of the enzyme reached a value of 2.3 × 103. In addition, oxidation of 1,2-propanediol catalyzed by the PQQ-dependent alcohol dehydrogenase proceeded enantioselectively to yield L-lactic acid.

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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