JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
·
2013
·
IF 2.823
Jian-Yong Zheng,Jia-Yu Wu,Yin-Jun Zhang,Zhao Wang
The mycelium of Aspergillus oryzae WZ007 was successfully developed to kinetic resolution of ( R , S )-ethyl-2-(4-hydroxyphenoxy) propanoate (( R , S )-EHPP) for production of ( R )-ethyl-2-(4-hydroxyphenoxy) propanoate (( R )-EHPP). The key biocatalytic process parameters (pH, temperature, rotation speed and substrate concentration) were optimized. Under the optimum conditions, the optical purity of ( R )-EHPP was improved up to >99% when the conversion was above 49%. A. oryzae WZ007 whole-cell lipase exhibited high reaction capacity, enantioselectivity and good reusability. The tolerable substrate concentration was 0.5 mol/L, and dry mycelium of A. oryzae WZ007 maintains over 80% of its initial activity after eight repeating cycles. Therefore the enzymatic preparation of ( R )-EHPP route was suitable for industrial application.
研究领域:
生物化学
·
微生物学
·
制药工程
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DOI
高影响因子
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
·
2025
·Vol. 61
·期 2
·338-345
·
IF 0.9
Li Chonglong,Lai Caiyun,Zhan Murong,Zhao Xiaona,Dong Wenyuan,Liu Jiaqi,Wang Peibiao
A novel helical poly(phenyl isocyanide) bearing an ( R,R )-(‒)-1,2-diaminocyclohexane pendant (poly- 2 200 ) was designed and synthesized. Helical poly- 2 200 showed an excellent catalytic performance in the asymmetric aldol reaction between cyclohexanone and 2-(trifluoromethyl)benzaldehyde in ethanol: the reaction product had an enantiomeric excess ( ee ) of 87.8%.
研究领域:
有机化学
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催化化学
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DOI
高影响因子
CHINESE JOURNAL OF POLYMER SCIENCE
·
2015
·Vol. 33
·期 12
·1713-1720
·
IF 1.835
Shao Jun,Liu Yan-long,Xiang Sheng,Bian Xin-chao,Sun Jing-ru,Li Gao,Chen Xue-si,Hou Hao-qing
In this study, the poly(L-lactide)/poly(D-lactide) (PLLA/PDLA) blends with different optical purities of PLLA and various molecular weights of PDLA are prepared by solution mixing, and the stereocomplex formation and phase separation behaviors of these blends are investigated. Results reveal that optical purity and molecular weight do not vary the crystal structure of PLA stereocomplex (sc) and homochiral crystallites (hc). As the optical purity increasing in the blends, the melting temperature of sc ( T
sc ) and the content of sc (Δ H
sc ) increased, while the melting temperature of hc ( T
hm ) hardly changes, although the content of hc (Δ H
hm ) decreased gradually. The T
sc and Δ H
sc are also enhanced as the molecular weight of PDLA reduces, and the Δ H
hm reduces rapidly even though the T
hm does not vary apparently. With lower optical purities of PLLA and higher molecular weights of PDLA, three types of crystals form in the blends, i.e. , PLA sc, PLLA hc and PDLA hc. As molecular weight decreases and optical purity enhances, the crystal phase decreases to two (sc and PDLA hc), and one (sc) finally. This investigation indicates that the phase separation behavior between PLLA and PDLA in the PLLA/PDLA blends not only depends on molecular weights, but also relies on the optical purities of polymers.
研究领域:
材料科学
·
高分子化学
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DOI
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2014
·
IF 0.697
Chuan-Zhu Gao,Tian-Shuai Wang,Jia Chen,Fan Fei,Ji Chen,Yan Zhang,Bo Yang
A novel and efficient method has been developed for the chiral resolution and separation from cis-cyclohexane-1,2-diamine of (±)-cyclohexane-1,2-diamine, which reacts with xylaric acid, a substitute for tartaric acid. This method provides (1R,2R)-cyclohexane-1,2-diamine, and (1S,2S)-cyclohexane-1,2-diamine and cis-cyclohexane-1,2-diamine in good yield with high optical purity.
研究领域:
有机化学
·
药物化学
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DOI
高影响因子
International Journal of Polymeric Materials and Polymeric Biomaterials
·
2018
·
IF 2.127
Baojiao Gao,Yanbin Li,Lulu Chen
The surface imprinted material of one single enantiomer of ibuprofen ((S)-ibuprofen) was successfully prepared using the novel surface imprinting technique of synchronously graft/crosslinking-polymerizing and molecule imprinting. Micron sized-silica gel particles as matrix were first modified with coupling agent γ-mercaptopropyl trimethoxysilane (MPMS), obtaining MPMS-SiO2 particles, on which there was a great deal of mercapto group (‒SH). Hydroxyethyl methylacrylate (HEMA) as functional monomer and dibenzoyl peroxide (BPO) as initiator were dissolved into 1,2-dichloroethane (DCE), and HEMA molecules are automatically combined around (S)-ibuprofen molecules by right of multi-site hydrogen bonds, forming self-assembly complex. A surface-initiating system of ‒SH/BPO was constituted at the interface between MPMS-SiO2 particles and DCE solution. The free radicals produced on the surfaces of MPMS-SiO2 particles initiated HEMA molecules around (S)-ibuprofen molecules to produce graft/crosslinking-polymerization on the surfaces of SiO2 particles. At the same time, (S)-ibuprofen molecules were wrapped in the cross-linked networks so that the surface-imprinting of (S)-ibuprofen was realized, forming (S)-ibuprofen surface imprinted particles ((S)-IBU-SIP). The enantiomeric recognition and resolution properties of (S)-IBU-SIP particles were investigated. The experimental results show that (S)-IBU-SIP particles have excellent enantiodiscrimination property and enantioseparation ability. The binding capacity of (S)-IBU-SIP particles for (S)-ibuprofen gets up to 177 mg g−1, and the selectivity coefficient of (S)-IBU-SIP particles for (S)-ibuprofen relative to (R)-ibuprofen is 5.03. For the ibuprofen raceme solution, after solid phase extraction by (S)-IBU-SIP particles, the optical purity (ee value of (S)-ibuprofen) of the eluent reaches up to 82.5%, whereas the optical purity (ee value of (R)-ibuprofen) of the supernatant is 44.2%.
研究领域:
药物化学
·
分析化学
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产品关联
DOI
高影响因子
JOURNAL OF APPLIED POLYMER SCIENCE
·
2017
·Vol. 134
·期 17
·
IF 1.86
Yanmei Guo,Jun Shao,Haoqing Hou
Linear poly( d -lactide) (PDLA) with various molecular weights is synthesized and incorporated into commercial poly( l -lactide) (PLLA) with different optical purities. And then, the crystallization, mechanical and thermal properties of the PLLA and PLLA/PDLA cast films are investigated. In the PLLA and PDLA/PLLA specimens with lower optical purity, few homochiral crystallites (HC) form in all the specimens and only a small amount of PLA stereocomplex crystallites (SC) are observed in the blends. The elongation at break of all the specimens is extraordinary high, >300%. Dynamic mechanical analyses indicate that the destruction temperature increases at first, and then depresses as enlarging the molecular weight of PDLA in these blends. For the PLLA and PLLA/PDLA with higher optical purity, more content of HC develops in neat PLLA, and both SC and HC produce in the PLLA/PDLA specimens. However, the strains of neat specimens and binary blends are much lower than that of specimens with lower optical purity. The specimens with higher optical purity exhibit higher destruction temperatures and lower loss factors. The high content of crystals (SC and HC) would act as the physical cross-linking points and provide a key factor to impede the deformation of neat PLLA and binary blends during stretching, which should result in the fragile behavior of the PLLA and PLLA/PDLA blends with higher optical purity. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134 , 44730.
研究领域:
材料科学
·
高分子化学
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产品关联
DOI
高影响因子
JOURNAL OF BIOTECHNOLOGY
·
2019
·
IF 3.163
Fei Peng,Ying Zhao,Fang-Zhou Li,Xiao-Yang Ou,Ying-Jie Zeng,Min-Hua Zong,Wen-Yong Lou
The asymmetric resolution of racemic 1-phenyl-1,2-ethanediol (PED) to ( S )-PED by Kurthia gibsonii SC0312 ( K. gibsonii SC0312) was conducted in a biphasic system comprised of an organic solvent and aqueous phosphate buffer. The impacts of organic solvents on the whole cell catalytic activity, metabolic activity, membrane integrity, and material distribution were first evaluated. The results showed that all organic solvents, except for dibutyl phthalate, showed a detrimental effect on the metabolic activity of the cells, especially for those with low log P values. All organic solvents were capable of changing the membrane permeability and membrane integrity of the cells. Moreover, some organic solvents showed a good extraction of the oxidation product. Finally, a high yield of 47.7 % of ( S )-PED was obtained by the asymmetric resolution of racemic PED using K. gibsonii SC0312 in a biphasic system under the optimal conditions: racemic PED 120 mM, temperature 35 °C, reaction time 6 h, 180 rpm, and a volume ratio of dibutyl phthalate to aqueous phosphate buffer of 1:1. The optical purity of ( S )-PED increased from 51.3 % to >99 %. This work described an efficient approach to improve reaction efficiency, and constructed a highly effective biphasic reaction system for the fabrication of ( S )-PED via K. gibsonii SC0312.
研究领域:
生物化学
·
微生物学
·
有机合成
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产品关联
DOI
PubMed
高影响因子
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
·
2019
·Vol. 35
·期 5
·792-798
·
IF 1.071
Dong Lu,Xu Yongkai,Zhang Yun,Sun Aijun,Hu Yunfeng
Bacillus sp. DL-2 was isolated from the deep sea of the Western Pacific and further utilized as novel biocatalysts to efficiently asymmetrically hydrolyze (±)-1-phenylethyl acetate. After the optimization of hydrolytic reactions, chiral chemicals ( R )-1-phenylethanol and ( S )-1-phenylethyl acetate were obtained with high optical purities (96% and 99.8%, respectively). Our research is about the asymmeric hydrolysis of (±)-1-phenylethyl acetate using whole-cell biocatalysts. In addition, the optical purity of ( S )-1-phenylethyl acetate generated through the kinetic resolution of (±)-1-phenylethyl acetate using the whole-cells of Bacillus sp. DL-2 was the highest report so far. Using the whole cells of deep sea bacterium Bacillus sp. DL-2 as the biocatalysts is an environmentally friendly method and will play critical roles in industrial asymmetric synthesis.
研究领域:
生物化学
·
工业微生物学
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DOI
高影响因子
ADVANCED SYNTHESIS & CATALYSIS
·
2016
·Vol. 358
·期 18
·2923-2928
·
IF 6.453
Peiyuan Yao,Yunfeng Cui,Shanshan Yu,Yuncheng Du,Jinhui Feng,Qiaqing Wu,Dunming Zhu
An efficient multi-enzyme cascade reaction for the synthesis of ( R )- or ( S )-2-hydroxybutyric acid [( R )- or ( S )-2-HB] from l -threonine was developed by using recombinant Escherichia coli cells expressing separately or co-expressing l -threonine deaminase from Escherichia coli K-12 ( ilvA ), formate dehydrogenase (FDH) from Candida boidinii and l -lactate dehydrogenase ( l -LDH) from Oryctolagus cuniculus or d -lactate dehydrogenase ( d -LDH) from Staphylococcus epidermidis ATCC 12228. Up to 750 mM of l -threonine were completely transformed to ( R )- or ( S )-2-HB in optically pure form (>99% ee ) with high isolated yields. This one-pot multi-enzyme transformation provides a new practical method for the synthesis of these important optically pure compounds.
研究领域:
生物化学
·
合成生物学
·
代谢工程
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产品关联
DOI
高影响因子
RSC Advances
·
2018
·Vol. 8
·期 53
·30512-30519
·
IF 2.936
Jian-Xiu Li,Yan-Yan Huang,Xian-Rui Chen,Qi-Shi Du,Jian-Zong Meng,Neng-Zhong Xie,Ri-Bo Huang
Acetoin is an important platform chemical with a variety of applications in foods, cosmetics, chemical synthesis, and especially in the asymmetric synthesis of optically active pharmaceuticals. It is also a useful breath biomarker for early lung cancer diagnosis. In order to enhance production of optical (S)-acetoin and facilitate this building block for a series of chiral pharmaceuticals derivatives, we have developed a systematic approach using in situ-NADH regeneration systems and promising diacetyl reductase. Under optimal conditions, we have obtained 52.9 g L−1 of (S)-acetoin with an enantiomeric purity of 99.5% and a productivity of 6.2 g (L h)−1. The results reported in this study demonstrated that the production of (S)-acetoin could be effectively improved through the engineering of cofactor regeneration with promising diacetyl reductase. The systematic approach developed in this study could also be applied to synthesize other optically active α-hydroxy ketones, which may provide valuable benefits for the study of drug development.
研究领域:
生物催化
·
药物化学
·
代谢工程
·
生物技术
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产品关联
DOI
PubMed
高影响因子
Frontiers in Bioengineering and Biotechnology
·
2022
·
IF 6.064
Jing Li,Jian Lu,Zhilin Ma,Jianxiu Li,Xianrui Chen,Mengxue Diao,Nengzhong Xie
2,3,5,6-Tetramethylpyrazine (TMP) is an active pharmaceutical ingredient originally isolated from Ligusticum wallichii for curing cardiovascular and cerebrovascular diseases and is widely used as a popular flavoring additive in the food industry. Hence, there is a great interest in developing new strategies to produce this high-value compound in an ecological and economical way. Herein, a cost-competitive combinational approach was proposed to accomplish green and high-efficiency production of TMP. First, microbial cell factories were constructed to produce acetoin (3-hydroxy-2-butanone, AC), an endogenous precursor of TMP, by introducing a biosynthesis pathway coupled with an intracellular NAD + regeneration system to the wild-type Escherichia coli . To further improve the production of ( R )-AC, the metabolic pathways of by-products were impaired or blocked stepwise by gene manipulation, resulting in 40.84 g/L ( R )-AC with a high optical purity of 99.42% in shake flasks. Thereafter, an optimal strain designated GXASR11 was used to convert the hydrolysates of inexpensive feedstocks into ( R )-AC and achieved a titer of 86.04 g/L within 48 h in a 5-L fermenter under optimized fermentation conditions. To the best of our knowledge, this is the highest ( R )-AC production with high optical purity (≥98%) produced from non-food raw materials using recombinant E . coli . The supernatant of fermentation broth was mixed with diammonium phosphate (DAP) to make a total volume of 20 ml and transferred to a high-pressure microreactor. Finally, 56.72 g/L TMP was obtained in 3 h via the condensation reaction with a high conversion rate (85.30%) under optimal reaction conditions. These results demonstrated a green and sustainable approach to efficiently produce high-valued TMP, which realized value addition of low-cost renewables.
研究领域:
药学
·
生物技术
·
代谢工程
·
可持续化学
·
微生物学
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产品关联
DOI
PubMed
高影响因子
BIOCATALYSIS AND BIOTRANSFORMATION
·
2019
·
IF 1.627
Lu Dong,Yongkai Xu,Yun Zhang,Aijun Sun,Yunfeng Hu
Chiral 1-phenylethanol and its ester derivative are important chiral chemicals in diverse industries and the preparation of those optically pure enantiomers is of great importance. One bacterium, Bacillus sp. DL-2, whose extracellular proteases could efficiently asymmetrically hydrolyse (±)-1-phenylethyl acetate, was isolated from the deep sea of the Western Pacific. After the immobilization of extracellular proteases and the optimization of enzymatic reactions, (R)-1-phenylethanol was prepared with the enantiomeric excess (e.e.) being 97% and the yield being 41%, respectively. The optimal resolution reaction condition for the preparation of (R)-1-phenylethanol using immobilized extracellular proteases was found to be 5-mM (±)-1-phenylethyl acetate, 360 mg/mL immobilized extracellular proteases, pH 6.5, and 20 °C for 2 h. (S)-1-phenylethyl acetate was generated through enzymatic kinetic resolution with the e.e. being as high as 99% and the yield being 71%, respectively. The optimal resolution reaction condition for the preparation of (S)-1-phenylethyl acetate was found to be 2.5-mM (±)-1-phenylethyl acetate, 440 mg/mL immobilized extracellular proteases, pH 7.5, and 35 °C for 10 h. Our report is the first report about the kinetic resolution of (±)-1-phenylethyl acetate using proteases and the enantio-preference of the proteases was found to be the same as those of most other esterases/lipases. Also notably, the optical purity of (S)-1-phenylethyl acetate generated through kinetic resolution using the proteases of Bacillus sp. DL-2 was the highest report so far. Proteases from deep-sea Bacillus sp. DL-2 are new contributions to the biocatalyst library for the preparation of valuable chiral alcohols and chiral esters through kinetic resolution.
研究领域:
生物催化
·
生物化学
·
微生物学
·
手性化学
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）