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Daojiang Yan, Qibin Chen, Jie Gao, Jian Bai, Bingyu Liu, Yalong Zhang, Le Zhang, Chen Zhang, Yi Zou, Youcai Hu
Fumiquinazolines are multicyclic peptidyl alkaloids where FAD-dependent oxidases are main tailing redox enzymes in their biosynthesis. Here, we characterized the use of an α-KG/Fe(II)-dependent dioxygenase (α-KGD) as a new strategy in Nature to increase structural complexity in fumiquinazolines biosynthesis by elucidating the concise three enzymes biosynthetic pathway of heptacyclical alanditrypinone (1). Further genome mining led to the discovery of additional gene cluster with α-KGD and trimodular NRPS as partner, which generates diverse fumiquinazolines...
February 14, 2019: Organic Letters
Yuka Ito, Junko Okuda-Shimazaki, Wakako Tsugawa, Noya Loew, Isao Shitanda, Chi-En Lin, Jeffrey La Belle, Koji Sode
Faradaic electrochemical impedance spectroscopy (faradaic EIS) is an attractive measurement principle for biosensors. However, there have been no reports on sensors employing direct electron transfer (DET)-type redox enzymes based on faradaic EIS principle. In this study, we have attempted to construct the 3rd-generation faradaic enzyme EIS sensor, which used DET-type flavin adenine dinucleotide (FAD) dependent glucose dehydrogenase (GDH) complex, to elucidate its characteristic properties as well as to investigate its potential application as the future immunosensor platform...
January 16, 2019: Biosensors & Bioelectronics
Dan Li, Ning Zhao, Bing-Jing Guo, Xi Lin, Shuang-Lin Chen, Shu-Zhen Yan
Hypocrellin A (HA) is a perylenequinone (PQ) isolated from Shiraia bambusicola that shows antiviral and antitumor activities, but its application is limited by the low production from wild fruiting body. A gene overexpressing method was expected to augment the production rate of HA in S. bambusicola. However, the application of this molecular biology technology in S. bambusicola was impeded by a low genetic transformation efficiency and little genomic information. To enhance the plasmid transformant ratio, the Polyethylene Glycol-mediated transformation system was established and optimized...
February 2019: Journal of Microbiology / the Microbiological Society of Korea
Clare F Megarity
Enzymes' inherent chirality confers their exquisite enantiomeric specificity and makes their use as green alternatives to chiral metal complexes or chiral organocatalysts invaluable to the fine chemical industry. The most prevalent way to alter enzyme activity in terms of regioselectivity and stereoselectivity for both industry and fundamental research is to engineer the enzyme(1-5). In a recent article by Keinänen et al , published in Bioscience Reports 2018, Controlling the Regioselectivity and Stereoselectivity of FAD-dependent Polyamine Oxidases with the use of Amine-attached Guide Molecules as Conformational Modulators , an inverse approach was presented which focuses on the manipulation of the enzyme substrate rather than the enzyme(6)...
January 30, 2019: Bioscience Reports
Taiki Nagano, Shunsuke Yamao, Anju Terachi, Hidetora Yarimizu, Haruki Itoh, Ryoko Katasho, Kosuke Kawai, Akio Nakashima, Tetsushi Iwasaki, Ushio Kikkawa, Shinji Kamada
d-amino acid oxidase (DAO) is a flavin adenine dinucleotide (FAD)-dependent oxidase metabolizing neutral and polar d-amino acids. Unlike l-amino acids, the amounts of d-amino acids in mammalian tissues are extremely low, and therefore, little has been investigated regarding the physiological role of DAO. We have recently identified DAO to be up-regulated in cellular senescence, a permanent cell cycle arrest induced by various stresses, such as persistent DNA damage and oxidative stress. Because DAO produces reactive oxygen species (ROS) as byproducts of substrate oxidation and the accumulation of ROS mediates the senescence induction, we explored the relationship between DAO and senescence...
February 2019: Life science alliance
Kareen H Veldmann, Hannah Minges, Norbert Sewald, Jin-Ho Lee, Volker F Wendisch
Halogenated compounds, like 7-chloro-L-tryptophan, are important intermediates or components of bioactive substances relevant for the pharmaceutical, chemical and agrochemical industries. About 20 % of all pharmaceutical small molecule drugs and around 30 % of all active compounds in agrochemistry are halogenated. Chemical halogenation procedures usually are characterized by the use of hazardous or even highly toxic chemicals. Recently, a biocatalytic process for L-tryptophan halogenation at the gram-scale using FAD-dependent halogenase and NADH-dependent flavin reductase enzymes has been described...
December 20, 2018: Journal of Biotechnology
Xuan Yun, Qian Zhang, Meinan Lv, Hai Deng, Zixin Deng, Yi Yu
3-Hydroxypicolinic acid (3-HPA) is an important pyridine building block of bacterial secondary metabolites. Although the main biosynthetic pathways of these metabolites have been identified and well characterized, the enzymatic mechanism underlying the biosynthesis of 3-HPA has yet to be elucidated. In this work, we successfully reconstituted the complete biosynthetic pathway of 3-HPA in vitro. We showed that an l-lysine 2-aminotransferase, a two-component monooxygenase, and a FAD-dependent dehydrogenase are required to convert l-lysine to 3-HPA...
December 19, 2018: Organic & Biomolecular Chemistry
Keqiang Fan, Qian Zhang
Angucyclines are one of the largest families of aromatic polyketides with various chemical structures and bioactivities. Decades of studies have made it easy for us to depict the picture of their early biosynthetic pathways. Two families of oxygenases, the FAD-dependent oxygenases and the ring opening oxygenases, contribute to the formation of some unique skeletons of atypical angucyclines. The FAD-dependent oxygenases involved in the biosynthetic gene clusters of typical angucyclines catalyze two hydroxylation reactions at C-12 and C-12b of prejadomycin, while their homolog JadH in jadomycin gene cluster catalyze the C-12 hydroxylation and 4a,12b-dehydration reactions of prejadomycin, which leads to the production of dehydrorabelomycin, a common intermediate during the biosynthesis of atypical angucyclines...
December 2018: Synthetic and Systems Biotechnology
Inyoung Lee, Noya Loew, Wakako Tsugawa, Kazunori Ikebukuro, Koji Sode
Continuous glucose monitoring (CGM) systems are most important in the current Type I diabetes care and as component for the development of artificial pancreas systems because the amount of insulin being supplied is calculated based on the CGM results. Therefore, to stably and accurately control the blood glucose level, CGM should be stable and accurate for a long period. We have been engaged in the biomolecular engineering and application of FAD dependent glucose dehydrogenase complex (FADGDH) which is capable of direct electron transfer...
January 15, 2019: Biosensors & Bioelectronics
Seiya Tsujimura
In this review, I present the main highlights of my works in the development of bioelectrocatalysis, which can be used in widespread applications, particularly for the design of biosensor and biofuel cells. In particular, I focus on research progress made in two key bioelectrocatalytic reactions: glucose oxidation by flavin adenine dinucleotide-dependent glucose dehydrogenase and oxygen reduction by bilirubin oxidase. I demonstrate the fundamental principles of bioelectrocatalysis and the requirements for enhancing the catalytic performance, including the choice of a mediator of redox reactions, immobilization, and electrode materials...
October 1, 2018: Bioscience, Biotechnology, and Biochemistry
Risa Nofiani, Kate de Mattos-Shipley, Karen E Lebe, Li-Chen Han, Zafar Iqbal, Andrew M Bailey, Christine L Willis, Thomas J Simpson, Russell J Cox
Strobilurins from fungi are the inspiration for the creation of the β-methoxyacrylate class of agricultural fungicides. However, molecular details of the biosynthesis of strobilurins have remained cryptic. Here we report the sequence of genomes of two fungi that produce strobilurins and show that each contains a biosynthetic gene cluster, which encodes a highly reducing polyketide synthase with very unusual C-terminal hydrolase and methyltransferase domains. Expression of stpks1 in Aspergillus oryzae leads to the production of prestrobilurin A when the fermentation is supplemented with a benzoyl coenzyme A (CoA) analogue...
September 26, 2018: Nature Communications
Joanna C Sadler, Andrew Currin, Douglas B Kell
Directed evolution enables the improvement and optimisation of enzymes for particular applications and is a valuable tool for biotechnology and synthetic biology. However, studies are often limited in their scope by the inability to screen very large numbers of variants to identify improved enzymes. One class of enzyme for which a universal, operationally simple ultra-high throughput (>106 variants per day) assay is not available is flavin adenine dinucleotide (FAD) dependent oxidases. The current high throughput assay involves a visual, colourimetric, colony-based screen, however this is not suitable for very large libraries and does not enable quantification of the relative fitness of variants...
September 24, 2018: Analyst
Luca Giacinto Iacovino, Francesca Magnani, Claudia Binda
The first crystal structure of mammalian monoamine oxidases (MAOs) was solved in 2002; almost 65 years after, these FAD-dependent enzymes were discovered and classified as responsible for the oxidation of aromatic neurotransmitters. Both MAO A and MAO B feature a two-domain topology characterized by the Rossmann fold, interacting with dinucleotide cofactors, which is intimately associated to a substrate-binding domain. This globular body is endowed with a C-terminal α-helix that anchors the protein to the outer mitochondrial phospholipid bilayer...
November 2018: Journal of Neural Transmission
Thomas Heine, Willem J H van Berkel, George Gassner, Karl-Heinz van Pée, Dirk Tischler
Flavoprotein monooxygenases create valuable compounds that are of high interest for the chemical, pharmaceutical, and agrochemical industries, among others. Monooxygenases that use flavin as cofactor are either single- or two-component systems. Here we summarize the current knowledge about two-component flavin adenine dinucleotide (FAD)-dependent monooxygenases and describe their biotechnological relevance. Two-component FAD-dependent monooxygenases catalyze hydroxylation, epoxidation, and halogenation reactions and are physiologically involved in amino acid metabolism, mineralization of aromatic compounds, and biosynthesis of secondary metabolites...
August 2, 2018: Biology
Tuomo A Keinänen, Nikolay Grigorenko, Alex R Khomutov, Qingqiu Huang, Anne Uimari, Leena Alhonen, Mervi T Hyvönen, Jouko Vepsäläinen
Enzymes generally display strict stereospecificity and regioselectivity for their substrates. Here by using FAD-dependent human acetylpolyamine oxidase (APAO), human spermine (Spm) oxidase (SMOX) and yeast polyamine oxidase (Fms1), we demonstrate that these fundamental properties of the enzymes may be regulated using simple guide molecules, being either covalently attached to polyamines or used as a supplement to the substrate mixtures. APAO, which naturally metabolizes achiral N 1 -acetylated polyamines, displays aldehyde-controllable stereospecificity with chiral 1-methylated polyamines, like (R)- and (S)- 1-methylspermidine (1,8-diamino-5-azanonane) (1-MeSpd)...
August 31, 2018: Bioscience Reports
Ying Zhao, Xin Li, Feng Wang, Xunchao Zhao, Yuqiao Gao, Changjiang Zhao, Lin He, Zuotong Li, Jingyu Xu
Glycerol-3-phosphate dehydrogenase (GPDH) catalyzes the formation of glycerol-3-phosphate, and plays an essential role in glycerolipid metabolism and in response to various stresses in different species. In this study, six ZmGPDH genes were obtained by a thorough search against maize genome, and designated as ZmGPDH1-6, respectively. The structural and evolutionary analyses showed that the ZmGPDHs family had typical conserved domains and similar protein structures as the known GPDHs from other plant species...
2018: PloS One
Kevin Sea, Jerry Lee, Daniel To, Berniece Chen, Matthew H Sazinsky, Edward J Crane
Within the family of pyridine nucleotide disulfide oxidoreductase (PNDOR), enzymes are a group of single-cysteine containing FAD-dependent reductases that utilize a tightly bound coenzyme A to assist in the NAD(P)H-dependent reduction of di-, per-, and polysulfide substrates in bacteria and archaea. For many of these homodimeric enzymes, it has proved difficult to determine the substrate specificity and metabolic function based on sequence and genome analysis alone. Coenzyme A-disulfide reductase (CoADR) isolated from Pyrococcus horikoshii ( ph CoADR) reduces Co-A per- and polysulfides, but, unlike other highly homologous members of this group, is a poor CoA disulfide reductase...
July 2018: FEBS Open Bio
Ethan G Stoddard, Regan F Volk, James P Carson, Cecilia M Ljungberg, Taylor A Murphree, Jordan N Smith, Natalie C Sadler, Anil K Shukla, Charles Ansong, Aaron T Wright
Lung diseases and disorders are a leading cause of death among infants. Many of these diseases and disorders are caused by premature birth and underdeveloped lungs. In addition to developmentally related disorders, the lungs are exposed to a variety of environmental contaminants and xenobiotics upon birth that can cause breathing issues and are progenitors of cancer. In order to gain a deeper understanding of the developing lung, we applied an activity-based chemoproteomics approach for the functional characterization of the xenometabolizing cytochrome P450 enzymes, active ATP and nucleotide binding enzymes, and serine hydrolases using a suite of activity-based probes (ABPs)...
August 3, 2018: Journal of Proteome Research
Jineetkumar Gawad, Chandrakant Bonde
Tuberculosis has proved harmful to the entire history of mankind from past several decades. Decaprenyl-phosphoryl-ribose 2'-epimerase (DprE1) is a recent target which was identified in 2009 but unfortunately it is neither explored nor crossed phase II. In past several decades few targets were identified for effective antitubercular drug discovery. Resistance is the major problem for effective antitubercular drug discovery. Arabinose is constituent of mycobacterium cell wall. Biosynthesis of arabinose is FAD dependant two step epimerisation reaction which is catalysed by DprE1 and DprE2 flavoprotein enzymes...
June 23, 2018: Chemistry Central Journal
Tayaba Ismail, Hyun-Kyung Lee, Chowon Kim, Taejoon Kwon, Tae Joo Park, Hyun-Shik Lee
The lysine-specific histone demethylase 1A (KDM1A) was the first demethylase to challenge the concept of the irreversible nature of methylation marks. KDM1A, containing a flavin adenine dinucleotide (FAD)-dependent amine oxidase domain, demethylates histone 3 lysine 4 and histone 3 lysine 9 (H3K4me1/2 and H3K9me1/2). It has emerged as an epigenetic developmental regulator and was shown to be involved in carcinogenesis. The functional diversity of KDM1A originates from its complex structure and interactions with transcription factors, promoters, enhancers, oncoproteins, and tumor-associated genes (tumor suppressors and activators)...
June 19, 2018: Epigenetics & Chromatin
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