BIOTECHNOLOGY LETTERS
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2020
·Vol. 42
·期 8
·1501-1511
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IF 1.977
Chang Ya-Wen,Zhang Jian-Dong,Yang Xiao-Xiao,Li Jing,Gao Li-Li,Huang Shuang-Ping,Guo Xing-Mei,Zhang Cao-Feng,Chang Hong-Hong,Xu Jian-He
Objectives To screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols. Results A new strain named Arthrobacter sp. TYUT010-15 with the ( R )-selective deamination activity of cyclic β-amino alcohol has been isolated from nature via a high throughput solid-phase screening method. The reaction conditions of TYUT010-15 were optimized. Using the resting cell of TYUT010-15 as the catalyst, kinetic resolution of trans -2-aminocyclopentanol, trans -2-aminocyclohexanol and cis -1-amino-2-indanol was carried out to afford (1 S , 2 S )- trans -2-aminocyclopentanol, (1 S , 2 S )- trans -2-aminocyclohexanol and (1 R , 2 S )- cis -1-amino-2-indanol in > 99% ee and 49.6–50% conversion. Four aromatic β-amino alcohols and two amines were also resolved, ( S )-β-amino alcohols and ( R )-amines were obtained in > 99% ee. Preparation experiment was conducted with 200 mM (23.2 g L −1 ) racemic trans -2-aminocyclohexanol, yielding the desired (1 S , 2 S )- trans -2-aminocyclohexanol in 40% isolated yield, > 99% ee and 5.8 g L −1 d −1 space time yields. Conclusions This study provides a high throughput solid-phase method for screening of bacteria with cyclic amino alcohol deamination activity and a first example for practical preparation of chiral cyclic β-amino alcohol by Arthrobacter sp. TYUT010-15.
研究领域:
微生物学
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有机化学
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生物催化
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手性化学
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DOI
PubMed
高影响因子
CHINESE JOURNAL OF CATALYSIS
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2013
·
IF 1.304
Ming Jin,Dan Zhao,Guozhen He,Yao Tong,Shiqing Han
An efficient method has been developed for the N -arylation of a variety of water-soluble amino alcohols (1.2 mmol) with aryl iodides (1.0 mmol) in water under CuI-catalyzed conditions. The reaction was conducted via substrate-promoted action and did not require an additional ligand or phase-transfer catalyst, and afforded the desired N -aryl amines in acceptable to excellent yields (64%–93%) under mild reaction conditions with a small excess of the amino alcohol.
研究领域:
有机化学
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合成化学
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DOI
高影响因子
Catalysis Science & Technology
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2020
·Vol. 10
·期 17
·5945-5952
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IF 5.721
Hongyue Wang,Ge Qu,Jun-Kuan Li,Jun-An Ma,Jinggong Guo,Yuchen Miao,Zhoutong Sun
Chiral amino alcohols are essential building blocks for the pharmaceutical industry, and are widely present in natural and synthetic bioactive compounds. Amine dehydrogenases (AmDHs) can asymmetrically reduce prochiral ketones with low-cost ammonia to chiral amines and water as by-products, using NAD(P)H as a cofactor under mild conditions, but hydroxy ketones with formation of chiral hydroxy amines have rarely been investigated. In this study, six new bacterial AmDHs derived from amino acid dehydrogenases (AADHs) were identified by data mining, and five out of the six enzymes were able to efficiently reduce 1-hydroxybutan-2-one (1a) to (S)-2-aminobutan-1-ol ((S)-2a) with 19–99% conversions and 99% ee. The five AmDHs were purified and biochemically characterized for reductive amination activity towards substrate 1a with the optimal pH at 8.5 or 9.0 and the optimal temperature at 45 °C, 50 °C or 55 °C, and provided reductive amination of a broad range of prochiral α-hydroxy ketones, and even of a model β-hydroxy ketone leading to β-hydroxy amine with 99% ee. Our study expands the toolbox of AmDHs in the synthesis of chiral amino alcohols.
研究领域:
生物化学
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合成生物学
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酶工程
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DOI
高影响因子
Catalysts
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2020
·Vol. 10
·期 12
·1419
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IF 3.52
Li-Hua Du,Miao Xue,Meng-Jie Yang,Yue Pan,Ling-Yan Zheng,Zhi-Min Ou,Xi-Ping Luo
An efficient method for the preparation of β-amino alcohols catalyzed by lipase TL IM fromThermomyces lanuginosusin a continuous-flow reactor was developed. The eco-friendly biocatalyst combined with continuous-flow reaction technology displayed high efficiency in the synthesis of β-amino alcohols. The benign reaction conditions (35 °C) and short residence time (20 min), together with the use of low cost and readily available starting materials, make this synthetic approach a promising alternative to current β-amino alcohol synthesis.Keywords:enzymatic synthesis;β-amino alcohols;reactor;epoxides;ring-opening reaction
研究领域:
生物化学
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有机合成
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绿色化学
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产品关联
DOI
高影响因子
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY
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2016
·Vol. 181
·期 3
·972-985
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IF 1.606
Wu Hua-Lei,Zhang Jian-Dong,Zhang Chao-Feng,Fan Xiao-Jun,Chang Hong-Hong,Wei Wen-Long
Four uncharacterized ω-transaminases (ωTAs) from Pseudomonas putida NBRC 14164 have been identified and cloned from the pool of fully sequenced genomes. The genes were functionally expressed in Escherichia coli BL21, and the enzymes were purified and characterized. Four TAs showed highly ( S )-selective ωTA activity and converted ( S )-α-methylbenzylamine and pyruvate to acetophenone and l -Ala. The maximum activity of cloned enzymes was in the pH range of 8.0– 8.5 (Pp36420), 8.5 –9. 5 (Pp21050), 9 .0– 9.5 (PpspuC), and 9.5 –1 0 . 5 (PpbauA), and the optimal temperatures were at 35 °C (Pp36420, Pp21050, and PpspuC) and 50 °C (PpbauA), respectively, with K
M of 161.3 mM (Pp21050), 136.7 mM (PpbauA), 398.5 mM (Pp36420), and 130.9 mM (PpspuC) and yielding a catalytic efficiency k
cat / K
M of 0.015, 0.003, 0.012, and 0.023 mM −1 s −1 . Several racemic amines and amino alcohols were resolved by the cloned ωTAs; perfect conversions (48–50 %) were obtained by at least one enzyme, and the residual substrates were left with 97–99 % ee. Kinetic resolution of racemic phenylglycinol was done with PpspuC in a 100-mL scale. Enaniomeric excess of ( S )-phenylglycinol reached 99 % with 45 % isolated yield. The high enantioselectivity and large substrate spectra of the cloned PpTAs showed an attractive potency for biotechnology application in production of chiral amines and amino alcohols.
研究领域:
生物化学
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酶工程
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生物技术
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DOI
PubMed
高影响因子
Journal of CO2 Utilization
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2018
·
IF 5.503
Xiaoyun Li,Jiexi Ke,Junwei Wang,Chen Liang,Maoqing Kang,Yuhua Zhao,Qifeng Li
In this work, CO 2 was chemically fixed by reacting with 1, 4-butanediol diglycidyl ether in the presence of a basic polystyrene resin catalyst. Under the 100% conversion of 1, 4-butanediol diglycidyl ether, five-membered cyclocarbonate with a selectivity of 98.5% was obtained. The cyclocarbonate was then reacted with an excess of 1, 2-ethylenediamine and the product was characterized by Fourier transform infrared spectrometer and nuclear magnetic resonance spectrometer. The results confirmed the successful synthesis of NH 2 terminated product with a selectivity of 98.9%, accompanied by the formation of hydroxyls on β-C to the carbonyl groups, which can be regarded as a new amino-alcohol. Further, the obtained amino-alcohol was applied for the preparation of polyurethane urea as chain extender in a prepolymer way. Since the reactivity of isocyanate with NH 2 is much faster than that with OH, the OH groups can be maintained in the system and hence strengthen the hydrogen bonding in polyurethane urea, which endows the materials with some unique properties. Comparing with the polyurethanes yielded from 1, 6-hexanediamine and 1, 6-hexanediol, polyurethane urea synthesized from the new amino-alcohol possessed better water/solvents resistance, considerable mechanical and thermal properties.
研究领域:
化学工程
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材料科学
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产品关联
DOI
高影响因子
Journal of CO2 Utilization
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2019
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IF 5.189
Xiaoyun Li,Jiexi Ke,Junwei Wang,Maoqing Kang,Yuhua Zhao,Qifeng Li,Chen Liang
A series of novel amino-alcohol curing agents for PU adhesives were synthesized from CO 2 , glycidyl ether and diamine through carbonation and amination reactions. By physically evaluating the compounds through FT-IR and 1 H NMR spectroscopy and mechanically analyzing the adhesives through T-peel strength tests, the raw materials have successfully been transformed into curing agents and the curing agents were found to endow the adhesives with specific structures and unique properties. For PVC bonding, compared to the traditional curing agents HDA and HDO, the T-peel strength and medium resistance from the novel amino-alcohol compounds improved. Further analysis revealed distinction in mechanical properties for different curing agents, the trifunctional curing agent exhibited the largest tensile strength and hardness. Moreover, thermal analysis of the adhesives demonstrated the considerable thermal stability to those prepared from HDA and HDO.
研究领域:
材料科学
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化学工程
✓ 已验证
产品关联
DOI
高影响因子
ACS Omega
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2025
·
IF 4.3
Tianfu Wu,Wei Song,Jing Wu,Jian Wen,Wanqing Wei,Liming Liu
Chiral amino alcohols are vital in many biologically active molecules and natural products and are crucial building blocks for the pharmaceutical industry. However, the chemosynthesis of chiral amino alcohols, particularly bichiral amino alcohols, faces challenges related to chemoselectivity and enantioselectivity. Here, a dual-enzyme cascade pathway for the synthesis of bichiral amino alcohols through difunctionalization, exhibiting both high chemo- and stereoselectivity, was proposed for the first time. Among them, NADPH-dependent meso-diaminopyrimidate dehydrogenase from Proteus vulgaris (PvDAPDH) exhibited (R)-selective reductive amination activity, converting ketones into chiral amines; natural glucose dehydrogenase from Bacillus megaterium (BmGDH) not only facilitated NADPH regeneration but also catalyzed the reductive hydroxylation of ketones to chiral alcohols. Second, the rational design of the rate-limiting enzyme PvDAPDH generated the mutant M4 with increased specific activity and catalytic efficiency (kcat/Km) for 16a up to 3.2- and 10.3-fold, respectively, compared to the wild type. Additionally, the yield of mutant M4 for 1a–16a increased by 1.1- to 37-fold compared to the wild type. Finally, two high-value bichiral amino alcohols (14b and 16b) were asymmetrically synthesized from the corresponding bietone via a one-pot dual-enzyme cascade, exhibiting excellent stereoselectivity (dr ≥ 98:2). These findings provide a potential biosynthetic pathway for the green synthesis of bichiral amino alcohols and complement existing synthetic methods.
研究领域:
生物化学
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合成生物学
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制药工程
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DOI
PubMed
高影响因子
Energy Storage Materials
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2024
·
IF 18.9
Kuo Wang,Tong Qiu,Lu Lin,Hongtu Zhan,Xiao-Xia Liu,Xiaoqi Sun
Zn anode experiences dendrite issues in aqueous Zn batteries. They result from uneven Zn 2+ flux and Sand behavior depending on the current density. Herein, the amino alcohol of 2,2′,2′′-nitrilotriethanol (NTE) additive with chelation ability is introduced to achieve stable and parallel Zn deposition. NTE preferentially adsorbs on Zn surface, which chelates with Zn 2+ at interface upon geometry transformation. It not only homogenizes Zn 2+ flux to inhibit dendrites at low current densities, but also supply sufficient Zn 2+ to delay Sand behavior at high current densities. Parallel growth of Zn hexagonal plates is realized. Thus, Zn plating/stripping in symmetric cells at 10 mA cm −2 reaches >1600 h cycle life with the addition of 2.5% NTE in the ZnSO 4 electrolyte, corresponding to a high cumulative plated capacity of 8.5 Ah cm −2 . At the conditions of 5 °C or 70% depth of discharge, the lifespans of symmetric cells also extend to 6977 h and 230 h, respectively. In anode free full cells, a Zn 2+ pre-inserted V 6 O 13 ·H 2 O cathode retains 250 mAh g −1 capacity after 300 cycles at 6 A g −1 , superior to 83 mAh g −1 with NTE free electrolyte.
研究领域:
材料科学
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电化学
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产品关联
DOI
高影响因子
SYNTHETIC COMMUNICATIONS
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2012
·
IF 1.062
Xi'an Chen,Huayue Wu,Shun Wang,Shaoming Huang
Nano-TiO2 is an effective heterogeneous catalyst for the ring opening of epoxides with aromatic amines to afford β-amino alcohols in good to excellent yields at room temperature under solvent-free conditions. It was found that the catalyst is recyclable, and the activity of the catalyst was not weakened markedly even after several reaction cycles. In addition, the catalytic activity of TiO2 strongly depends on particle size or surface area.
研究领域:
化学
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催化材料科学
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DOI
高影响因子
CARBOHYDRATE RESEARCH
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2012
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IF 2.332
Hai-Min Shen,Hong-Bing Ji
Inspired by β-CD, a macrocyclic oligomers of d -(+)-glucopyranose and a renewable material, which could be obtained from starch, that can promote a lot of organic reactions in water, a green solvent, several amino alcohol-modified β-CDs CD-1 to CD-7 were synthesized in the yields of 36–61%. Their conformations in vacuum and in aqueous solution were optimized by quantum calculation. Their complexes with sodium molybdate prepared in situ were characterized by 1 H NMR and were applied in the asymmetric oxidation of thioanisole. Their performance in inducing enantioselectivity was investigated in detail. For the optimal one, CD-1, moderate enantioselectivity (56% ee) was achieved in aqueous CH 3 COONa–HCl buffer solution (pH 7.0). The abilities of CD-1 to CD-7 to induce asymmetry are highly dependent on the pH value of the reaction medium and the structure of the modifying group. The origin of the moderate enantioselectivity and the reaction mechanism were investigated with the aid of 1 H ROESY NMR studies and quantum calculation. The moderate enantioselectivity was attributed to the two different binding models between CD-1 and thioanisole, which could be defined as intramolecular catalysis and intermolecular catalysis, in which intramolecular catalysis gave ( S )-methyl phenyl sulfoxide and intermolecular catalysis gave ( R , S )-methyl phenyl sulfoxide.
研究领域:
有机化学
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绿色化学
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催化化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY A
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2018
·
IF 3.716
Yang Zhang,Shanshan Wang,Jianguang Luo,Yaolan Lin,Xiao Xu,Chao Han,Lingyi Kong
Synephrine, a chiral adrenergic agonist, exists as R - (more active) and S -enantiomers (less active) that are difficult to separate because of their alkalinity and high polarity. Herein, we show that although this enantioseparation can hardly be achieved by high-performance liquid chromatography, acceptable preparative separation can be realized using high-speed counter-current chromatography (HSCCC) and pH-zone-refining counter-current chromatography (CCC) under optimal conditions. Specifically, 23.0 mg of S -synephrine and 25.0 mg of R -synephrine were isolated from 60.0 mg of racemic synephrine by conventional HSCCC, while 70.0 mg of S -synephrine and 69.0 mg of R -synephrine were obtained from 200.0 mg of racemic synephrine by pH-zone-refining CCC. The pH-zone-refining CCC was identified as the most efficient enantioseparation technique for synephrine and can be applied for the preparative enantioseparation of other β-amino alcohols.
研究领域:
药学
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分析化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
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