Category: 6290-03-5

Kim, Taeho; Stogios, Peter J.; Khusnutdinova, Anna N.; Nemr, Kayla; Skarina, Tatiana; Flick, Robert; Joo, Jeong Chan; Mahadevan, Radhakrishnan; Savchenko, Alexei; Yakunin, Alexander F. published the artcile< Rational engineering of 2-deoxyribose-5-phosphate aldolases for the biosynthesis of (R)-1,3-butanediol>, Name: (R)-Butane-1,3-diol, the main research area is engineering deoxyribosephosphate aldolase Bacillus crystal structure butanediol; 1,3-butanediol; 2-deoxyribose-5-phosphate aldolase (DERA); BH1352; Escherichia coli (E. coli); acetaldehyde condensation; aldo-keto reductase; biotechnology; crystal structure; protein engineering; site-directed mutagenesis.

Carbon-carbon bond formation is one of the most important reactions in biocatalysis and organic chem. In nature, aldolases catalyze the reversible stereoselective aldol addition between two carbonyl compounds, making them attractive catalysts for the synthesis of various chems. In this work, we identified several 2-deoxyribose-5-phosphate aldolases (DERAs) having acetaldehyde condensation activity, which can be used for the biosynthesis of (R)-1,3-butanediol (1,3BDO) in combination with aldo-keto reductases (AKRs). Enzymic screening of 20 purified DERAs revealed the presence of significant acetaldehyde condensation activity in 12 of the enzymes, with the highest activities in BH1352 from Bacillus halodurans, TM1559 from Thermotoga maritima, and DeoC from Escherichia coli. The crystal structures of BH1352 and TM1559 at 1.40-2.50 Å resolution are the first full-length DERA structures revealing the presence of the C-terminal Tyr (Tyr224 in BH1352). The results from structure-based site-directed mutagenesis of BH1352 indicated a key role for the catalytic Lys155 and other active-site residues in the 2-deoxyribose-5-phosphate cleavage and acetaldehyde condensation reactions. These experiments also revealed a 2.5-fold increase in acetaldehyde transformation to 1,3BDO (in combination with AKR) in the BH1352 F160Y and F160Y/M173I variants. The replacement of the WT BH1352 by the F160Y or F160Y/M173I variants in E. coli cells expressing the DERA + AKR pathway increased the production of 1,3BDO from glucose five and six times, resp. Thus, our work provides detailed insights into the mol. mechanisms of substrate selectivity and activity of DERAs and identifies two DERA variants with enhanced activity for in vitro and in vivo 1,3BDO biosynthesis.

Journal of Biological Chemistry published new progress about Bacillus halodurans (source of 2-deoxyribose-5-phosphate aldolase BH1352). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Name: (R)-Butane-1,3-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Liu, Yu; Cen, Xuecong; Liu, Dehua; Chen, Zhen published the artcile< Metabolic engineering of Escherichia coli for high-yield production of (R)-1,3-butanediol>, Safety of (R)-Butane-1,3-diol, the main research area is metabolic engineering Escherichia butanediol fed batch fermentation; 1,3-butanediol; Escherichia coli; cofactor engineering; enzyme screening; metabolic engineering.

1,3-Butanediol (1,3-BDO) is an important C4 platform chem. widely used as a solvent in cosmetics and a key intermediate for the synthesis of fragrances, pheromones, and pharmaceuticals. The development of sustainable bioprocesses to produce enantiopure 1,3-BDO from renewable bioresources by fermentation is a promising alternative to conventional chem. routes and has aroused great interest in recent years. Although two metabolic pathways have been previously established for the biosynthesis of (R)-1,3-PDO, the reported titer and yield are too low for cost-competitive production In this study, we report the combination of different metabolic engineering strategies to improve the production of (R)-1,3-BDO by Escherichia coli, including (1) screening of key pathway enzymes; (2) increasing NADPH supply by cofactor engineering; (3) optimization of fermentation conditions to divert more flux into 1,3-BDO pathway; (4) reduction of byproducts formation by pathway engineering. With these efforts, the best engineered E. coli strain can efficiently produce (R)-1,3-BDO with a yield of 0.6 mol/mol glucose, corresponding to 60% of the theor. yield. Besides, we also showed the feasibility of aerobically producing 1,3-BDO via a new pathway using 3-hydroxybutyrate as an intermediate.

ACS Synthetic Biology published new progress about Escherichia coli. 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Safety of (R)-Butane-1,3-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kim, Taeho; Stogios, Peter J.; Khusnutdinova, Anna N.; Nemr, Kayla; Skarina, Tatiana; Flick, Robert; Joo, Jeong Chan; Mahadevan, Radhakrishnan; Savchenko, Alexei; Yakunin, Alexander F. published the artcile< Rational engineering of 2-deoxyribose-5-phosphate aldolases for the biosynthesis of (R)-1,3-butanediol>, Name: (R)-Butane-1,3-diol, the main research area is engineering deoxyribosephosphate aldolase Bacillus crystal structure butanediol; 1,3-butanediol; 2-deoxyribose-5-phosphate aldolase (DERA); BH1352; Escherichia coli (E. coli); acetaldehyde condensation; aldo-keto reductase; biotechnology; crystal structure; protein engineering; site-directed mutagenesis.

Carbon-carbon bond formation is one of the most important reactions in biocatalysis and organic chem. In nature, aldolases catalyze the reversible stereoselective aldol addition between two carbonyl compounds, making them attractive catalysts for the synthesis of various chems. In this work, we identified several 2-deoxyribose-5-phosphate aldolases (DERAs) having acetaldehyde condensation activity, which can be used for the biosynthesis of (R)-1,3-butanediol (1,3BDO) in combination with aldo-keto reductases (AKRs). Enzymic screening of 20 purified DERAs revealed the presence of significant acetaldehyde condensation activity in 12 of the enzymes, with the highest activities in BH1352 from Bacillus halodurans, TM1559 from Thermotoga maritima, and DeoC from Escherichia coli. The crystal structures of BH1352 and TM1559 at 1.40-2.50 Å resolution are the first full-length DERA structures revealing the presence of the C-terminal Tyr (Tyr224 in BH1352). The results from structure-based site-directed mutagenesis of BH1352 indicated a key role for the catalytic Lys155 and other active-site residues in the 2-deoxyribose-5-phosphate cleavage and acetaldehyde condensation reactions. These experiments also revealed a 2.5-fold increase in acetaldehyde transformation to 1,3BDO (in combination with AKR) in the BH1352 F160Y and F160Y/M173I variants. The replacement of the WT BH1352 by the F160Y or F160Y/M173I variants in E. coli cells expressing the DERA + AKR pathway increased the production of 1,3BDO from glucose five and six times, resp. Thus, our work provides detailed insights into the mol. mechanisms of substrate selectivity and activity of DERAs and identifies two DERA variants with enhanced activity for in vitro and in vivo 1,3BDO biosynthesis.

Journal of Biological Chemistry published new progress about Bacillus halodurans (source of 2-deoxyribose-5-phosphate aldolase BH1352). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Name: (R)-Butane-1,3-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Liu, Yu; Cen, Xuecong; Liu, Dehua; Chen, Zhen published the artcile< Metabolic engineering of Escherichia coli for high-yield production of (R)-1,3-butanediol>, Safety of (R)-Butane-1,3-diol, the main research area is metabolic engineering Escherichia butanediol fed batch fermentation; 1,3-butanediol; Escherichia coli; cofactor engineering; enzyme screening; metabolic engineering.

1,3-Butanediol (1,3-BDO) is an important C4 platform chem. widely used as a solvent in cosmetics and a key intermediate for the synthesis of fragrances, pheromones, and pharmaceuticals. The development of sustainable bioprocesses to produce enantiopure 1,3-BDO from renewable bioresources by fermentation is a promising alternative to conventional chem. routes and has aroused great interest in recent years. Although two metabolic pathways have been previously established for the biosynthesis of (R)-1,3-PDO, the reported titer and yield are too low for cost-competitive production In this study, we report the combination of different metabolic engineering strategies to improve the production of (R)-1,3-BDO by Escherichia coli, including (1) screening of key pathway enzymes; (2) increasing NADPH supply by cofactor engineering; (3) optimization of fermentation conditions to divert more flux into 1,3-BDO pathway; (4) reduction of byproducts formation by pathway engineering. With these efforts, the best engineered E. coli strain can efficiently produce (R)-1,3-BDO with a yield of 0.6 mol/mol glucose, corresponding to 60% of the theor. yield. Besides, we also showed the feasibility of aerobically producing 1,3-BDO via a new pathway using 3-hydroxybutyrate as an intermediate.

ACS Synthetic Biology published new progress about Escherichia coli. 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Safety of (R)-Butane-1,3-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhang, Xin; Ang, Esther Cai Xia; Yang, Ziqi; Kee, Choon Wee; Tan, Choon-Hong published the artcile< Synthesis of chiral sulfinate esters by asymmetric condensation>, Application of C4H10O2, the main research area is alc sulfinate pentanidium catalyst enantioselective condensation; sulfinate ester preparation.

Here a straightforward access to enantioenriched sulfinate esters via asym. condensation of prochiral sulfinates and alcs. using pentanidium as an organocatalyst was reported. This study successfully coupled a wide range of sulfinates and bioactive alcs. stereoselectively. The initial sulfinates was prepared from existing sulfone and sulfonamide drugs and the resulting sulfinate esters were versatile for transformations to diverse chiral sulfur pharmacophores. Through late-stage diversification 11,12 of celecoxib and other drug derivatives, was demonstrate the viability of this unified approach towards sulfur stereogenic centers.

Nature (London, United Kingdom) published new progress about Condensation reaction catalysts (stereoselective). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Application of C4H10O2.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhao, Jie; Ji, Shufang; Guo, Chenxi; Li, Haijing; Dong, Juncai; Guo, Ping; Wang, Dingsheng; Li, Yadong; Toste, F. Dean published the artcile< A heterogeneous iridium single-atom-site catalyst for highly regioselective carbenoid O-H bond insertion>, Recommanded Product: (R)-Butane-1,3-diol, the main research area is hydroxy ester preparation regioselective; alc diazo ester insertion iridium catalyst.

A strategy for selective carbenoid O-H insertion that exploits an engineered heterogeneous iridium single-atom catalyst, thus providing opportunities for organic transformations by merging material science and catalysis was reported. This catalytic protocol delivers excellent selectivities (up to 99:1) for the functionalization of aliphatic over phenolic O-H bonds R1C6H4CH(R2)C(O)OMe (R1 = H, 4-Br, 3-F, 4-Me; R2 = cyclohexyl, Bn, 2,2,2-trifluoroethyl, 1-methyl-1H-indol-3-yl, etc.), whereas the analogus homogeneous catalyst, Ir(ttp)COCl (ttp = 5,10,15,20-tetra-p-tolylporphyrinato), provided modest preferences. D.-functional-theory calculations suggest that the site-selectivity derives from the lower oxidation state of the iridium metal center in the heterogeneous catalyst and its impact on the absorption energies of the reactants. These results showcase an example of a heterogeneous single-atom catalyst providing superior site-selectivity and provide a complementary strategy to address challenges in catalysis for organic synthesis.

Nature Catalysis published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Recommanded Product: (R)-Butane-1,3-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhang, Leilei; Xu, Yue; Lou, Boxuan; Qin, Xiaolan; Zhang, Lijuan; Liu, Xijian; Yuan, Haikuan; Zhang, Yan; Rohani, Sohrab; Lu, Jie published the artcile< Effect of Additives on Preferential Crystallization for the Chiral Resolution of Citrulline: Experimental, Statistical, and Molecular Dynamics Simulation Studies>, Reference of 6290-03-5, the main research area is preferential crystallization chiral resolution citrulline.

The molar fraction solubilities of L-, D-, and DL-citrulline were first determined in aqueous solutions with different concentrations of (R)-1,3-butanediol from 283.15 to 328.15 K under 101.3 kPa using the gravimetric method. Then, based on solid-state characterizations such as powder X-ray diffraction (PXRD), Fourier transform IR (FTIR) spectroscopy, thermal gravity anal. (TGA), differential scanning calorimetry (DSC), and ternary phase diagram, the nature of crystalline DL-citrulline was considered to be a racemic compound Then, the rates and parameters of primary nucleation of three species in mixtures of water and (R)-1,3-butanediol were exptl. derived through the classical nucleation theory (CNT). After that, topol. electrostatic potentials and radial distribution functions were analyzed for exploring the intermol. interactions between the mols., and the Yasuoka-Matsumoto (YM) method was employed to simulate the nucleation process. However, the calculated nucleation rates by YM were shown to be 2 orders of magnitude greater than those derived through CNT. Finally, the effect of additives on the appearance probability (P) of racemic and enantiomeric nuclei from the same DL-citrulline solutions at a supersaturation ratio of 2.63 was statistically investigated from 140 nucleation experiments It was interestingly found that there was only a minor difference between the appearance probabilities of both enantiomeric crystals among 20 batches of nucleations in the absence of additives; however, in the presence of additives, enantiomeric crystals with the same chirality as the additives were totally inhibited, which were utilized for the chiral enrichment of the studied racemic system. By coupling the addition of additives and seeds, L-citrulline or D-citrulline crystals with optical purity above 99% can be produced with a yield up to 25.4% through chiral enrichment from an initial ee of 88%.

Crystal Growth & Design published new progress about Activation energy. 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Reference of 6290-03-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zu, Han; Zhang, Hui; Fan, Anwen; Gu, Jie; Nie, Yao; Luo, Pengjie; Xu, Yan published the artcile< Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by newly isolated Pichia kudriavzevii>, Application of C4H10O2, the main research area is butanediol asym reduction hydroxybutanone stereoselectivity Pichia biosynthesis sequence.

(R)-1,3-butanediol is an important pharmaceutical intermediate, and the synthesis of (R)-1,3-butanediol using green biol. methods has recently been of interest for industrial application. Here, a novel strain QC-1 that efficiently transforms 4-hydroxy-2-butanone to (R)-1,3-butanediol was isolated from soil samples. Based on morphol., physiol., and biochem. tests and 5.8S-internal transcribed spacer sequencing, the strain was identified as Pichia kudriavzevii QC-1. The reaction conditions were optimized to 35°C, pH 8.0, rotation speed 200 rpm, and 6:5 mass ratio of glucose to 4-hydroxy-2-butanone. Evaluation of the effects of 4-hydroxy-2-butanone concentrations on yield and cell survival rate showed that 85.60 g·L-1 product accumulated, with an enantiomeric excess of more than 99%, when 30 g·L-1 4-hydroxy-2-butanone was added at 0, 10, and 30 h in a 3-L bioreactor. Thus, strain QC-1 showed excellent catalytic activity and stereoselectivity for the synthesis of (R)-1,3-butanediol from 4-hydroxy-2-butanone.

Chinese Journal of Chemical Engineering published new progress about Concentration (condition). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Application of C4H10O2.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Yang, Zeyu; Fu, Hengwei; Ye, Wenjie; Xie, Youyu; Liu, Qinghai; Wang, Hualei; Wei, Dongzhi published the artcile< Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system>, Name: (R)-Butane-1,3-diol, the main research area is asym synthesis chiral alc propanol oxidation alc dehydrogenase; thermostatic bubble column reactor system alc dehydrogenase ketone reduction.

Alc. dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asym. synthesis of chiral alcs.; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the byproduct, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technol. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, volume/volume) concentration Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the byproduct acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcs. are synthesized at a high substrate loading (>150 g L-1) without adding external coenzymes. Among these, about 780 g L-1 (6 M) Et acetoacetate is completely converted into Et (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L-1 d-1 space-time yield. Mol. dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcs. on an industrial scale.

Catalysis Science & Technology published new progress about Alcohols, chiral Role: BPN (Biosynthetic Preparation), BIOL (Biological Study), PREP (Preparation). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Name: (R)-Butane-1,3-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Sun, Zhongwei; Li, Pan; Xu, Shijun; Li, Zi-Ying; Nomura, Yoshiaki; Li, Zimu; Liu, Xiaoyun; Zhang, Shaodong published the artcile< Controlled Hierarchical Self-Assembly of Catenated Cages>, SDS of cas: 6290-03-5, the main research area is controlled hierarchical self assembly catenated cage.

Constructing hierarchical superstructures to achieve comparable complexity and functions to proteins with four-level hierarchy is challenging, which relies on the elaboration of novel building blocks with complex structures. We present a series of catenated cages with unique structural complexity and tailorability. The rational design was realized as follows. A catenane of two sym. cages (CSC), CSC-1, with all rigid imine panels was converted to a catenane of two dissym. cages (CDC), CDC-1, with two exterior flexible amine panels, and CDC-5 was tailored from CDC-1 by introducing an addnl. Me group on each blade to increase lateral hindrance. CDC-1s with the most irregular and flexible configuration formed supramol. dimers, which self-organized into 3D continuous wavelike plank with a three-level hierarchy, previously undiscovered by conventional building blocks. A drastically different 3D triclinic crystalline phase with a four-level hierarchy and trigonal phase with a three-level hierarchy were constructed of distorted CSC-1s and the most sym. CDC-5s, resp. The wavelike plank exhibited the lowest order, and the triclinic phase had a lower order than the trigonal phase which had the highest order. It correlates with the configuration of the primary structures, namely, the most disordered shape of CDC-1, the low-order configuration of CSC-1, and the most ordered geometry of CDC-5. The catenated cages with subtle structural differences therefore provide a promising platform for the search of emerging hierarchical superstructures that might be applied to proton conductivity, ferroelectricity, and catalysis.

Journal of the American Chemical Society published new progress about Cage compounds Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, SDS of cas: 6290-03-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts