516-06-3Relevant articles and documents
Rational engineering ofAcinetobacter tandoiiglutamate dehydrogenase for asymmetric synthesis ofl-homoalanine through biocatalytic cascades
Diao, Shiqing,Jiang, Shuiqin,Liu, Yan,Sun, Yangyang,Wang, Hualei,Wang, Liuzhu,Wei, Dongzhi
, p. 4208 - 4215 (2021/06/30)
l-Homoalanine, a useful building block for the synthesis of several chiral drugs, is generally synthesized through biocascades using natural amino acids as cheap starting reactants. However, the addition of expensive external cofactors and the low efficiency of leucine dehydrogenases towards the intermediate 2-ketobutyric acid are two major challenges in industrial applications. Herein, a dual cofactor-dependent glutamate dehydrogenase fromAcinetobacter tandoii(AtGluDH) was identified to help make full use of the intracellular pool of cofactors when using whole-cell catalysis. Through reconstruction of the hydrophobic network between the enzyme and the terminal methyl group of the substrate 2-ketobutyric acid, the strict substrate specificity ofAtGluDH towards α-ketoglutarate was successfully changed, and the activity obtained by the most effective mutant (K76L/T180C) was 17.2 times higher than that of the wild-type protein. A three-enzyme co-expression system was successfully constructed in order to help release the mass transfer restriction. Using 1 Ml-threonine, which is close to the solubility limit, we obtained a 99.9% yield ofl-homoalanine in only 3.5 h without adding external coenzymes to the cascade, giving 99.9% ee and a 29.2 g L?1h?1space-time yield. Additionally, the activities of the engineeredAtGluDH towards some other hydrophobic amino acids were also improved to 1.1-11.2 fold. Therefore, the engineering design of some dual cofactor-dependent GluDHs could not only eliminate the low catalytic activity of unnatural substrates but also enhance the cofactor utilization efficiency of these enzymes in industrial applications.
Highly Efficient Synthesis of Amino Acids by Amination of Bio-Derived Hydroxy Acids with Ammonia over Ru Supported on N-Doped Carbon Nanotubes
Xie, Zhenbing,Chen, Bingfeng,Peng, Fangfang,Liu, Mingyang,Liu, Huizhen,Yang, Guanying,Han, Buxing
, p. 5683 - 5689 (2020/09/21)
The amino acids have extensive applications, and their productions from biomass-derived feedstocks are very attractive. In this work, the synthesis of amino acids by amination of bio-derived hydroxy acids with ammonia over different metallic nano-catalysts supported on various supports is studied. It is found that Ru nano-catalysts on the nitrogen-doped carbon nanotubes (Ru/N?CNTs) have an outstanding performance for the reaction. Different hydroxy acids can be catalytically converted into the corresponding amino acids with yields up to 70.0 % under mild conditions, which is higher than those reported. The reasons for the high efficiency of the catalyst are investigated, and the reaction pathway is proposed on the basis of control experiments.
Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines
Liu, Xiangyuan,Liu, Yang,Chai, Guobi,Qiao, Baokun,Zhao, Xiaowei,Jiang, Zhiyong
supporting information, p. 6298 - 6301 (2018/10/09)
With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.
Catalytic amino acid production from biomass-derived intermediates
Deng, Weiping,Wang, Yunzhu,Zhang, Sui,Gupta, Krishna M.,Hülsey, Max J.,Asakura, Hiroyuki,Liu, Lingmei,Han, Yu,Karp, Eric M.,Beckham, Gregg T.,Dyson, Paul J.,Jiang, Jianwen,Tanaka, Tsunehiro,Wang, Ye,Yan, Ning
, p. 5093 - 5098 (2018/05/23)
Amino acids are the building blocks for protein biosynthesis and find use in myriad industrial applications including in food for humans, in animal feed, and as precursors for bio-based plastics, among others. However, the development of efficient chemical methods to convert abundant and renewable feedstocks into amino acids has been largely unsuccessful to date. To that end, here we report a heterogeneous catalyst that directly transforms lignocellulosic biomass-derived α-hydroxyl acids into α-amino acids, including alanine, leucine, valine, aspartic acid, and phenylalanine in high yields. The reaction follows a dehydrogenation-reductive amination pathway, with dehydrogenation as the rate-determining step. Ruthenium nanoparticles supported on carbon nanotubes (Ru/CNT) exhibit exceptional efficiency compared with catalysts based on other metals, due to the unique, reversible enhancement effect of NH3 on Ru in dehydrogenation. Based on the catalytic system, a two-step chemical process was designed to convert glucose into alanine in 43% yield, comparable with the well-established microbial cultivation process, and therefore, the present strategy enables a route for the production of amino acids from renewable feedstocks. Moreover, a conceptual process design employing membrane distillation to facilitate product purification is proposed and validated. Overall, this study offers a rapid and potentially more efficient chemical method to produce amino acids from woody biomass components.
Catalytic Conversion of Alcohols to Carboxylic Acid Salts and Hydrogen with Alkaline Water
Sarbajna, Abir,Dutta, Indranil,Daw, Prosenjit,Dinda, Shrabani,Rahaman, S. M. Wahidur,Sarkar, Abheek,Bera, Jitendra K.
, p. 2786 - 2790 (2017/05/31)
A [RuH(CO)(py-NP)(PPh3)2]Cl (1) catalyst is found to be effective for catalytic transformation of primary alcohols, including amino alcohols, to the corresponding carboxylic acid salts and two molecules of hydrogen with alkaline water. The reaction proceeds via acceptorless dehydrogenation of alcohol, followed by a fast hydroxide/water attack to the metal-bound aldehyde. A pyridyl-type nitrogen in the ligand architecture seems to accelerate the reaction.
Structure and biosynthesis of xenoamicins from entomopathogenic xenorhabdus
Zhou, Qiuqin,Grundmann, Florian,Kaiser, Marcel,Schiell, Matthias,Gaudriault, Sophie,Batzer, Andreas,Kurz, Michael,Bode, Helge B.
supporting information, p. 16772 - 16779 (2014/01/06)
During the search for novel natural products from entomopathogenic Xenorhabdus doucetiae DSM17909 and X. mauleonii DSM17908 novel peptides named xenoamicins were identified in addition to the already known antibiotics xenocoumacin and xenorhabdin. Xenoamicins are acylated tridecadepsipeptides consisting of mainly hydrophobic amino acids. The main derivative xenoamicin A (1) was isolated from X. mauleonii DSM17908, and its structure elucidated by detailed 1 D and 2 D NMR experiments. Detailed MS experiments, also in combination with labeling experiments, confirmed the determined structure and allowed structure elucidation of additional derivatives. Moreover, the xenoamicin biosynthesis gene cluster was identified and analyzed in X. doucetiae DSM17909, and its participation in xenoamicin biosynthesis was confirmed by mutagenesis. Advanced Marfey's analysis of 1 showed that the absolute configuration of the amino acids is in agreement with the predicted stereochemistry deduced from the nonribosomal peptide synthetase XabABCD. Biological testing revealed activity of 1 against Plasmodium falciparum and other neglected tropical diseases but no antibacterial activity.
Biocatalytic asymmetric synthesis of unnatural amino acids through the cascade transfer of amino groups from primary amines onto keto acids
Park, Eul-Soo,Dong, Joo-Young,Shin, Jong-Shik
, p. 3538 - 3542 (2014/01/06)
Flee to the hills: An unfavorable equilibrium in the amino group transfer between amino acids and keto acids catalyzed by α-transaminases was successfully overcome by coupling with a ω-transaminase reaction as an equilibrium shifter, leading to efficient asymmetric synthesis of diverse unnatural amino acids, including L-tert-leucine and D-phenylglycine. Copyright
Meteorites as catalysts for prebiotic chemistry
Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto
, p. 16916 - 16922 (2014/01/06)
From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.
Ohmyungsamycins A and B: Cytotoxic and antimicrobial cyclic peptides produced by Streptomyces sp. from a volcanic island
Um, Soohyun,Choi, Tae Joon,Kim, Heegyu,Kim, Byung Yong,Kim, Seong-Hwan,Lee, Sang Kook,Oh, Ki-Bong,Shin, Jongheon,Oh, Dong-Chan
, p. 12321 - 12329 (2014/01/17)
Ohmyungsamycins A and B (1 and 2), which are new cyclic peptides, were isolated from a marine bacterial strain belonging to the Streptomyces genus collected from a sand beach on Jeju, a volcanic island in the Republic of Korea. Based on the interpretation of the NMR, UV, and IR spectroscopic and MS data, the planar structures of 1 and 2 were elucidated as cyclic depsipeptides bearing unusual amino acid units, including N-methyl-4-methoxytrytophan, β-hydroxyphenylalanine, and N,N-dimethylvaline. The absolute configurations of the α-carbons of the amino acid residues were determined using the advanced Marfey's method. The configurations of the additional stereogenic centers at the β-carbons of the threonine, N-methylthreonine, and β-hydroxyphenylalanine units were assigned by GITC (2,3,4,6-tetra-O-acetyl- β-d-glucopyranosyl isothiocyanate) derivatization and the modified Mosher's method. We have developed a new method utilizing PGME (phenylglycine methyl ester) derivatization coupled with chromatographic analysis to determine the absolute configuration of N,N-dimethylvaline. Our first successful establishment of the absolute configuration of N,N-dimethylvaline using PGME will provide a general and convenient analytical method for determining the absolute configurations of amino acids with fully substituted amine groups. Ohmyungsamycins A and B showed significant inhibitory activities against diverse cancer cells as well as antibacterial effects.
Method for the production of high-level soluble human recombinant interferon alpha in e. coli and vectors useful for such a production
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, (2009/01/20)
Method for the production of high-level soluble human recombinant interferon alpha protein (rhuIFNα) in E. coli and vectors useful for such a production. Said method comprises the steps of: (1) Transforming an E. coli selected in the group consisting of E. coli protease deficient host strains, and E. coli reductase deficient host strains, with a recombinant expression vector comprising the sequence encoding the glutathione-S-transferase (GST), a junction sequence including a recognition site for a specific protease and a sequence able to encode an interferon alpha (IFN alpha) protein under the control of an inducible promoter, said vector encoding a GST-IFN alpha fusion protein (2) Expressing said interferon alpha protein in conditions comprising the induction of the expression with 0.1 mM-0.5 mM IPTG and a growth temperature of 25° and/or 37°C, depending on said E. coli strain and (3) Isolating the expressed IFN alpha protein.
