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Journal articles on the topic 'Heterocyclic natural product biosynthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Meng, Song, Gong-Li Tang, and Hai-Xue Pan. "Enzymatic Formation of Oxygen-Containing Heterocycles in Natural Product Biosynthesis." ChemBioChem 19, no. 19 (2018): 2002–22. http://dx.doi.org/10.1002/cbic.201800225.

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2

Winand, Lea, Dustin Joshua Vollmann, Jacqueline Hentschel, and Markus Nett. "Characterization of a Solvent-Tolerant Amidohydrolase Involved in Natural Product Heterocycle Formation." Catalysts 11, no. 8 (2021): 892. http://dx.doi.org/10.3390/catal11080892.

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Heterocycles are important building blocks in pharmaceutical drugs and their enzymatic synthesis is attracting increasing interest. In recent years, various enzymes of the amidohydrolase superfamily were reported to catalyze heterocycle-forming condensation reactions. One of these enzymes, MxcM, is biochemically and kinetically characterized in this study. MxcM generates an imidazoline moiety in the biosynthesis of the natural product pseudochelin A, which features potent anti-inflammatory properties. The enzyme shows maximal activity at 50 °C and pH 10 as well as a kcat/Km value of 22,932 s−1

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3

Cogan, Dillon P., Graham A. Hudson, Zhengan Zhang, et al. "Structural insights into enzymatic [4+2] aza-cycloaddition in thiopeptide antibiotic biosynthesis." Proceedings of the National Academy of Sciences 114, no. 49 (2017): 12928–33. http://dx.doi.org/10.1073/pnas.1716035114.

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The [4+2] cycloaddition reaction is an enabling transformation in modern synthetic organic chemistry, but there are only limited examples of dedicated natural enzymes that can catalyze this transformation. Thiopeptides (or more formally thiazolyl peptides) are a class of thiazole-containing, highly modified, macrocyclic secondary metabolites made from ribosomally synthesized precursor peptides. The characteristic feature of these natural products is a six-membered nitrogenous heterocycle that is assembled via a formal [4+2] cycloaddition between two dehydroalanine (Dha) residues. This heteroan

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4

Gibson, Colin. "Preface." Pure and Applied Chemistry 84, no. 7 (2012): iv. http://dx.doi.org/10.1351/pac20128407iv.

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It is a privilege to act as the conference editor for this issue of Pure and Applied Chemistry. The 11 papers in this issue constitute selected contributions from the 23rd International Congress on Heterocyclic Chemistry, which was held in the Scottish Exhibition and Conference Centre in Glasgow between 31 July and 4 August 2011. This congress of the International Society of Heterocyclic Chemistry was attended by over 400 participants from over 40 different countries.The conference papers in this issue arise from plenary (Profs. Magid Abou-Gharbia and David O’Hagan), invited (Profs. Janine Cos

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5

Grünewald, Jan, and Mohamed A. Marahiel. "Chemoenzymatic and Template-Directed Synthesis of Bioactive Macrocyclic Peptides." Microbiology and Molecular Biology Reviews 70, no. 1 (2006): 121–46. http://dx.doi.org/10.1128/mmbr.70.1.121-146.2006.

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SUMMARY Non-ribosomally synthesized peptides have compelling biological activities ranging from antimicrobial to immunosuppressive and from cytostatic to antitumor. The broad spectrum of applications in modern medicine is reflected in the great structural diversity of these natural products. They contain unique building blocks, such as d-amino acids, fatty acids, sugar moieties, and heterocyclic elements, as well as halogenated, methylated, and formylated residues. In the past decades, significant progress has been made toward the understanding of the biosynthesis of these secondary metabolite

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6

Hemmerling, Franziska, and Frank Hahn. "Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides." Beilstein Journal of Organic Chemistry 12 (July 20, 2016): 1512–50. http://dx.doi.org/10.3762/bjoc.12.148.

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This review highlights the biosynthesis of heterocycles in polyketide natural products with a focus on oxygen and nitrogen-containing heterocycles with ring sizes between 3 and 6 atoms. Heterocycles are abundant structural elements of natural products from all classes and they often contribute significantly to their biological activity. Progress in recent years has led to a much better understanding of their biosynthesis. In this context, plenty of novel enzymology has been discovered, suggesting that these pathways are an attractive target for future studies.

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7

Nash, Robert J. "Natural product biosynthesis." New Phytologist 155, no. 1 (2002): 7. http://dx.doi.org/10.1046/j.1469-8137.2002.00449_4.x.

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8

Frankel, Brenda A., and Dewey G. McCafferty. "Profiling Natural Product Biosynthesis." Chemistry & Biology 11, no. 3 (2004): 290–91. http://dx.doi.org/10.1016/j.chembiol.2004.03.007.

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9

Tibrewal, Nidhi, and Yi Tang. "Biocatalysts for Natural Product Biosynthesis." Annual Review of Chemical and Biomolecular Engineering 5, no. 1 (2014): 347–66. http://dx.doi.org/10.1146/annurev-chembioeng-060713-040008.

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10

Liu, Hung-wen, and Tadhg Begley. "Natural product biosynthesis—a Renaissance." Current Opinion in Chemical Biology 17, no. 4 (2013): 529–31. http://dx.doi.org/10.1016/j.cbpa.2013.07.005.

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11

Tang, Man-Cheng, Yi Zou, Kenji Watanabe, Christopher T. Walsh, and Yi Tang. "Oxidative Cyclization in Natural Product Biosynthesis." Chemical Reviews 117, no. 8 (2016): 5226–333. http://dx.doi.org/10.1021/acs.chemrev.6b00478.

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12

Komor, Anna J., Andrew J. Jasniewski, Lawrence Que, and John D. Lipscomb. "Diiron monooxygenases in natural product biosynthesis." Natural Product Reports 35, no. 7 (2018): 646–59. http://dx.doi.org/10.1039/c7np00061h.

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13

Fecik, Robert A. "Natural product biosynthesis moves in vitro." Nature Chemical Biology 3, no. 9 (2007): 531–32. http://dx.doi.org/10.1038/nchembio0907-531.

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14

Gholami, Azra, Nathan De Geyter, Jacob Pollier, Sofie Goormachtig, and Alain Goossens. "Natural product biosynthesis in Medicago species." Natural Product Reports 31, no. 3 (2014): 356. http://dx.doi.org/10.1039/c3np70104b.

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15

Hubert, Catherine B., and Sarah M. Barry. "New chemistry from natural product biosynthesis." Biochemical Society Transactions 44, no. 3 (2016): 738–44. http://dx.doi.org/10.1042/bst20160063.

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Catalysts are a vital part of synthetic chemistry. However, there are still many important reactions for which catalysts have not been developed. The use of enzymes as biocatalysts for synthetic chemistry is growing in importance due to the drive towards sustainable methods for producing both bulk chemicals and high value compounds such as pharmaceuticals, and due to the ability of enzymes to catalyse chemical reactions with excellent stereoselectivity and regioselectivity. Such challenging transformations are a common feature of natural product biosynthetic pathways. In this mini-review, we d

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16

Neumann, Christopher S., Danica Galonić Fujimori, and Christopher T. Walsh. "Halogenation Strategies In Natural Product Biosynthesis." Chemistry & Biology 15, no. 2 (2008): 99–109. http://dx.doi.org/10.1016/j.chembiol.2008.01.006.

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17

O’Neill, Ellis. "Mining Natural Product Biosynthesis in Eukaryotic Algae." Marine Drugs 18, no. 2 (2020): 90. http://dx.doi.org/10.3390/md18020090.

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Eukaryotic algae are an extremely diverse category of photosynthetic organisms and some species produce highly potent bioactive compounds poisonous to humans or other animals, most notably observed during harmful algal blooms. These natural products include some of the most poisonous small molecules known and unique cyclic polyethers. However, the diversity and complexity of algal genomes means that sequencing-based research has lagged behind research into more readily sequenced microbes, such as bacteria and fungi. Applying informatics techniques to the algal genomes that are now available re

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18

Ding, Wei, Yongzhen Li, and Qi Zhang. "Substrate-Controlled Stereochemistry in Natural Product Biosynthesis." ACS Chemical Biology 10, no. 7 (2015): 1590–98. http://dx.doi.org/10.1021/acschembio.5b00104.

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19

Yonekura-Sakakibara, Keiko, and Kazuki Saito. "Functional genomics for plant natural product biosynthesis." Natural Product Reports 26, no. 11 (2009): 1466. http://dx.doi.org/10.1039/b817077k.

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20

Scherlach, Kirstin, and Christian Hertweck. "Triggering cryptic natural product biosynthesis in microorganisms." Organic & Biomolecular Chemistry 7, no. 9 (2009): 1753. http://dx.doi.org/10.1039/b821578b.

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21

Xu, Xianhao, Yanfeng Liu, Guocheng Du, Rodrigo Ledesma-Amaro, and Long Liu. "Microbial Chassis Development for Natural Product Biosynthesis." Trends in Biotechnology 38, no. 7 (2020): 779–96. http://dx.doi.org/10.1016/j.tibtech.2020.01.002.

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22

Thibodeaux, Christopher J., Charles E. Melançon, and Hung-wen Liu. "Unusual sugar biosynthesis and natural product glycodiversification." Nature 446, no. 7139 (2007): 1008–16. http://dx.doi.org/10.1038/nature05814.

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23

Thibodeaux, Christopher J, Charles E Melançon, and Hung-wen Liu. "Natural-Product Sugar Biosynthesis and Enzymatic Glycodiversification." Angewandte Chemie International Edition 47, no. 51 (2008): 9814–59. http://dx.doi.org/10.1002/anie.200801204.

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24

Winter, Jaclyn M., and Yi Tang. "Synthetic biological approaches to natural product biosynthesis." Current Opinion in Biotechnology 23, no. 5 (2012): 736–43. http://dx.doi.org/10.1016/j.copbio.2011.12.016.

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25

Strohl, William R. "Biochemical Engineering of Natural Product Biosynthesis Pathways." Metabolic Engineering 3, no. 1 (2001): 4–14. http://dx.doi.org/10.1006/mben.2000.0172.

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26

Yokoyama, Kenichi. "Radical Breakthroughs in Natural Product and Cofactor Biosynthesis." Biochemistry 57, no. 4 (2017): 390–402. http://dx.doi.org/10.1021/acs.biochem.7b00878.

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27

Micallef, Melinda L., Paul M. D'Agostino, Bakir Al-Sinawi, Brett A. Neilan, and Michelle C. Moffitt. "Exploring cyanobacterial genomes for natural product biosynthesis pathways." Marine Genomics 21 (June 2015): 1–12. http://dx.doi.org/10.1016/j.margen.2014.11.009.

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28

Moutiez, Mireille, Pascal Belin, and Muriel Gondry. "Aminoacyl-tRNA-Utilizing Enzymes in Natural Product Biosynthesis." Chemical Reviews 117, no. 8 (2017): 5578–618. http://dx.doi.org/10.1021/acs.chemrev.6b00523.

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29

Waldman, Abraham J., Tai L. Ng, Peng Wang, and Emily P. Balskus. "Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis." Chemical Reviews 117, no. 8 (2017): 5784–863. http://dx.doi.org/10.1021/acs.chemrev.6b00621.

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30

Scott, Thomas A., and Jörn Piel. "The hidden enzymology of bacterial natural product biosynthesis." Nature Reviews Chemistry 3, no. 7 (2019): 404–25. http://dx.doi.org/10.1038/s41570-019-0107-1.

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31

Kellner, Franziska, Jeongwoon Kim, Bernardo J. Clavijo, et al. "Genome-guided investigation of plant natural product biosynthesis." Plant Journal 82, no. 4 (2015): 680–92. http://dx.doi.org/10.1111/tpj.12827.

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32

Kim, Eunji, Bradley S. Moore, and Yeo Joon Yoon. "Reinvigorating natural product combinatorial biosynthesis with synthetic biology." Nature Chemical Biology 11, no. 9 (2015): 649–59. http://dx.doi.org/10.1038/nchembio.1893.

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33

Anarat-Cappillino, Gülbenk, and Elizabeth S. Sattely. "The chemical logic of plant natural product biosynthesis." Current Opinion in Plant Biology 19 (June 2014): 51–58. http://dx.doi.org/10.1016/j.pbi.2014.03.007.

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34

Skellam, Elizabeth. "Strategies for Engineering Natural Product Biosynthesis in Fungi." Trends in Biotechnology 37, no. 4 (2019): 416–27. http://dx.doi.org/10.1016/j.tibtech.2018.09.003.

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35

Skellam, Elizabeth. "Strategies for Engineering Natural Product Biosynthesis in Fungi." Trends in Biotechnology 37, no. 8 (2019): 916. http://dx.doi.org/10.1016/j.tibtech.2019.03.014.

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36

Dornisch, Elisabeth, Jakob Pletz, Ronald A. Glabonjat, et al. "Biosynthesis of the Enterotoxic Pyrrolobenzodiazepine Natural Product Tilivalline." Angewandte Chemie International Edition 56, no. 46 (2017): 14753–57. http://dx.doi.org/10.1002/anie.201707737.

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37

Yu, Dayu, Fuchao Xu, Jia Zeng, and Jixun Zhan. "Type III polyketide synthases in natural product biosynthesis." IUBMB Life 64, no. 4 (2012): 285–95. http://dx.doi.org/10.1002/iub.1005.

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38

Chevrette, Marc G., Karina Gutiérrez-García, Nelly Selem-Mojica, et al. "Evolutionary dynamics of natural product biosynthesis in bacteria." Natural Product Reports 37, no. 4 (2020): 566–99. http://dx.doi.org/10.1039/c9np00048h.

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We review known evolutionary mechanisms underlying the overwhelming chemical diversity of bacterial natural products biosynthesis, focusing on enzyme promiscuity and the evolution of enzymatic domains that enable metabolic traits.

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39

Cacho, Ralph A., and Yi Tang. "Bringing Protein Engineering and Natural Product Biosynthesis Together." Chemistry & Biology 20, no. 1 (2013): 3–5. http://dx.doi.org/10.1016/j.chembiol.2013.01.005.

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40

Bilyk, Oksana, and Andriy Luzhetskyy. "Metabolic engineering of natural product biosynthesis in actinobacteria." Current Opinion in Biotechnology 42 (December 2016): 98–107. http://dx.doi.org/10.1016/j.copbio.2016.03.008.

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41

Loeschcke, Anita, and Stephan Thies. "Engineering of natural product biosynthesis in Pseudomonas putida." Current Opinion in Biotechnology 65 (October 2020): 213–24. http://dx.doi.org/10.1016/j.copbio.2020.03.007.

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42

Belshaw, Peter J. "Quantifying Intermediates in Template-Directed Natural Product Biosynthesis." Chemistry & Biology 11, no. 3 (2004): 288–90. http://dx.doi.org/10.1016/j.chembiol.2004.03.008.

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43

Bernhardt, Peter, and Sarah E. O’Connor. "Opportunities for enzyme engineering in natural product biosynthesis." Current Opinion in Chemical Biology 13, no. 1 (2009): 35–42. http://dx.doi.org/10.1016/j.cbpa.2009.01.005.

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44

Pearsall, Sarah M., Christopher N. Rowley, and Alan Berry. "Advances in Pathway Engineering for Natural Product Biosynthesis." ChemCatChem 7, no. 19 (2015): 3078–93. http://dx.doi.org/10.1002/cctc.201500602.

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45

Tan, Gao-Yi, Zixin Deng, and Tiangang Liu. "Recent advances in the elucidation of enzymatic function in natural product biosynthesis." F1000Research 4 (December 4, 2015): 1399. http://dx.doi.org/10.12688/f1000research.7187.1.

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With the successful production of artemisinic acid in yeast, the promising potential of synthetic biology for natural product biosynthesis is now being realized. The recent total biosynthesis of opioids in microbes is considered to be another landmark in this field. The importance and significance of enzymes in natural product biosynthetic pathways have been re-emphasized by these advancements. Therefore, the characterization and elucidation of enzymatic function in natural product biosynthesis are undoubtedly fundamental for the development of new drugs and the heterologous biosynthesis of ac

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46

Tan, Gao-Yi, Zixin Deng, and Tiangang Liu. "Recent advances in the elucidation of enzymatic function in natural product biosynthesis." F1000Research 4 (February 25, 2016): 1399. http://dx.doi.org/10.12688/f1000research.7187.2.

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With the successful production of artemisinic acid in yeast, the promising potential of synthetic biology for natural product biosynthesis is now being realized. The recent total biosynthesis of opioids in microbes is considered to be another landmark in this field. The importance and significance of enzymes in natural product biosynthetic pathways have been re-emphasized by these advancements. Therefore, the characterization and elucidation of enzymatic function in natural product biosynthesis are undoubtedly fundamental for the development of new drugs and the heterologous biosynthesis of ac

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47

Dunbar, Kyle L., Daniel H. Scharf, Agnieszka Litomska, and Christian Hertweck. "Enzymatic Carbon–Sulfur Bond Formation in Natural Product Biosynthesis." Chemical Reviews 117, no. 8 (2017): 5521–77. http://dx.doi.org/10.1021/acs.chemrev.6b00697.

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48

Esquenazi, E., A. C. Jones, T. Byrum, P. C. Dorrestein, and W. H. Gerwick. "Temporal dynamics of natural product biosynthesis in marine cyanobacteria." Proceedings of the National Academy of Sciences 108, no. 13 (2011): 5226–31. http://dx.doi.org/10.1073/pnas.1012813108.

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49

Onaka, Hiroyasu, Yukiko Mori, Yasuhiro Igarashi, and Tamotsu Furumai. "Mycolic Acid-Containing Bacteria Induce Natural-Product Biosynthesis inStreptomycesSpecies." Applied and Environmental Microbiology 77, no. 2 (2010): 400–406. http://dx.doi.org/10.1128/aem.01337-10.

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ABSTRACTNatural products produced by microorganisms are important starting compounds for drug discovery. Secondary metabolites, including antibiotics, have been isolated from differentStreptomycesspecies. The production of these metabolites depends on the culture conditions. Therefore, the development of a new culture method can facilitate the discovery of new natural products. Here, we show that mycolic acid-containing bacteria can influence the biosynthesis of cryptic natural products inStreptomycesspecies. The production of red pigment byStreptomyces lividansTK23 was induced by coculture wi

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50

Hugelshofer, Cedric L., and Thomas Magauer. "Dyotropic rearrangements in natural product total synthesis and biosynthesis." Natural Product Reports 34, no. 3 (2017): 228–34. http://dx.doi.org/10.1039/c7np00005g.

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