Article
Chemistry, Physical
Jianxiong Zhao, Daniel Mendez-Sanchez, Rebecca Roddan, John M. Ward, Helen C. Hailes
Summary: The study demonstrates the use of wild-type NCS and selected variants with various ketones to access challenging non-natural THIAs. Some NCS variants were found to accept fused bicyclic ketones and diketones, providing new insights into the rational for this acceptance through in silico modeling.
Article
Biotechnology & Applied Microbiology
Man Zhang, Zheng-Yu Huang, Ying Su, Fei-Fei Chen, Qi Chen, Jian-He Xu, Gao-Wei Zheng
Summary: By utilizing the improved biocatalyst and using condensation reactions as the main strategy, the synthesis of 1-aryl-tetrahydroisoquinoline alkaloids with significant biological and pharmaceutical activity was achieved, yielding products with high conversion rate and optical purity.
BIORESOURCES AND BIOPROCESSING
(2023)
Article
Cell Biology
Xinyi Li, Qishuang Li, Xiang Jiao, Hao Tang, Yatian Cheng, Ying Ma, Guanghong Cui, Jinfu Tang, Yun Chen, Juan Guo, Luqi Huang
Summary: In this study, two functional StNCSs genes were identified and characterized from the Menispermaceae family plant Stephania tetrandra. These genes could catalyze the formation of (S)-norcoclaurine and provide genetic components for synthetic biology-based production of BIAs in yeast. The study also contributes to understanding the phylogenetic relationships and structure-function relationship of NCS genes involved in the origin and production of BIAs.
JOURNAL OF CELLULAR PHYSIOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Xiaozheng Wang, Dekun Kong, Tingting Huang, Fei Xu, Man-Cheng Tang, Zixin Deng, Shuangjun Lin
Summary: In this study, a new enzyme StnP2 was discovered to catalyze the biosynthesis of beta-Carboline alkaloids and exhibited catalytic activity towards various TH beta-C, highlighting the importance of flavoproteins.
ACS CHEMICAL BIOLOGY
(2022)
Review
Integrative & Complementary Medicine
Cao Ning, Wang Chang-Hong
Summary: This article reviews the latest research on the biosynthesis of natural compounds TIAs and BCAs, focusing on the role of strictosidine synthase in this process and the sources and substrate specificity of related compounds derived from strictosidine. The presence of six-bladed four-stranded beta-propeller folds in many organisms other than plants may indicate similar functions among different organisms. The expression of the strictosidine synthase gene has a significant impact on the production of various compounds, which are mainly used in plant cell suspension culture for the production of valuable drugs and biosynthesis in other carriers.
CHINESE JOURNAL OF NATURAL MEDICINES
(2021)
Article
Chemistry, Multidisciplinary
Remi Andres, Qian Wang, Jieping Zhu
Summary: A divergent asymmetric total synthesis of voacafricines A and B, hexacyclic monoterpene indole alkaloids, has been achieved by several key steps, including a catalyst-controlled asymmetric Pictet-Spengler reaction, oxidative cleavage, and intramolecular nucleophilic addition. The synthesis confirmed the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Haiting Yin, Qin Ma, Yushan Wang, Xiaoxia Gu, Zhijun Feng, Yunjun Wu, Ming Wang, Shaoyin Wang
Summary: The study presents a facile and efficient route to tetrahydro-beta-carbolines from 2-indolylmethyl azides and propargylic alcohols via acid-catalyzed dehydrative annulation reactions. The reaction involves a cascade sequence of Friedel-Crafts-type alkylation followed by intramolecular Click reaction, forming multiple chemical bonds in a single operation with excellent atom-economy and broad functional group tolerance.
Article
Chemistry, Medicinal
Ramil Y. Baiazitov, Hongyan Qi, Tamil Arasu, William Lennox, Liangxian Cao, Marla Weetall, Bansri Furia, Jin Zhuo, Soongyu Choi, Min Jung Kim, Josephine Sheedy, Thomas Davis, Young-Choon Moon
Summary: This paper describes a lead optimization campaign that led to the discovery of Emvododstat (PTC299), a highly potent DHODH inhibitor. Modulating the activity of this enzyme can be used to control diseases associated with rapid, out-of-control cell growth.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Remi Andres, Fenggang Sun, Qian Wang, Jieping Zhu
Summary: An asymmetric Pictet-Spengler reaction of alpha-ketoesters was developed, achieving high yields and ee values. The reaction mechanism was proposed to involve deprotonation of the pentahydro-beta-carbolinium ion as the rate- and enantioselectivity-determining step. This methodology was successfully applied in the enantioselective total synthesis of (+)-alstratine A, and the remeasurement of its [a](D) value revealed a correction in the initial report.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Plant Sciences
Raku Irie, Kei Miyako, Satoko Matsunaga, Ryuichi Sakai, Masato Oikawa
Summary: The structure of protoaculeine B, a marine peptide toxin, has been revised to a cis-1,3-disubstituted tetrahydro-beta-carboline framework. Two truncated model compounds were prepared using the one-step Pictet-Spengler reaction of tryptophan, which successfully reproduced the natural product's profiles and confirmed the appropriateness of the structure revision.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Multidisciplinary
Michael E. Pyne, Vincent J. J. Martin
Summary: This review outlines the increasing activity surrounding the production of natural, semisynthetic, and new-to-nature THIQ metabolites in engineered microbial systems, which has accelerated THIQ pathway discovery and engineering, and spurred the development of highly productive microbial strains.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiang Wang, Pinzhuo Ren, Gongping Gu, Zongyou Jiang, Bolin Xiang, Shi Tang, Ai-Qun Jia
Summary: An efficient and convenient method for the construction of diverse free (N-H)-benzazepinoindoles using Pd-catalyzed C(sp(2))-H imidoylative cyclization of 3-(2-isocyanobenzyl)-1H-indoles was developed. The reaction displays a broad substrate scope and can be scaled up, providing a practical route to valuable bioactive azepinoindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Qi-Wen Shen, Wei Wen, Qi-Xiang Guo
Summary: The first catalytic asymmetric cascade Heck-alkylation reaction of NH2-unprotected amino acid esters with N-(2-iodophenyl)allenamides is reported in this work. The reaction proceeds smoothly using a combining catalytic system comprising a chiral aldehyde, a chiral palladium complex, and the Lewis acid ZnCl2, giving optically active alpha-alkyl tryptophan derivatives in moderate to good yields and excellent enantioselectivities. The target products can be converted into other structurally complex chiral indoles without the loss of enantioselectivities.
Review
Chemistry, Multidisciplinary
Anup Biswas
Summary: The Pictet-Spengler reaction, a century-old technique for constructing aza-cycles, has been extensively researched using organocatalytic methods in the past two decades. The asymmetric variant of this reaction has gained significant attention due to the prevalence of enantioenriched polyheterocycles in natural products and bioactive molecules. This review focuses on the systematic and chronological assembly of enantioselective P-S reactions catalyzed by different types of organocatalysts, with an additional emphasis on mechanistic approaches to explain the asymmetric induction on the products. The importance of this conventional reaction is justified by the synthesis of various biologically and naturally relevant compounds, which are highlighted in this review.
Article
Chemistry, Medicinal
G. F. Sakhautdinova, I. M. Sakhautdinov, I. S. Nazarov, A. G. Mustafin, V. Vinogradova, M. S. Yunusov
Summary: New synthetic benzylisoquinoline-alkaloid analogs based on the diaryl ether hernandial were prepared under Pictet-Spengler reaction conditions.
CHEMISTRY OF NATURAL COMPOUNDS
(2022)
Article
Chemistry, Medicinal
Michael W. Mullowney, Eoghainin O. Hainmhire, Urszula Tanouye, Joanna E. Burdette, Van Cuong Pham, Brian T. Murphy
Article
Chemistry, Medicinal
Michael W. Mullowney, Chang Hwa Hwang, Andrew G. Newsome, Xiaomei Wei, Urszula Tanouye, Baojie Wan, Skylar Carlson, Nanthida Joy Barranis, Eoghainin O. hAinmhire, Wei-Lun Chen, Kalyanaraman Krishnamoorthy, John White, Rachel Blair, Hyunwoo Lee, Joanna E. Burdette, Pradipsinh K. Rathod, Tanya Parish, Sanghyun Cho, Scott G. Franzblau, Brian T. Murphy
ACS INFECTIOUS DISEASES
(2015)
Article
Chemistry, Multidisciplinary
Gabriel J. Lovinger, Mark D. Aparece, James P. Morken
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Review
Biochemistry & Molecular Biology
Michael W. Mullowney, Ryan A. McClure, Matthew T. Robey, Neil L. Kelleher, Regan J. Thomson
NATURAL PRODUCT REPORTS
(2018)
Article
Chemistry, Medicinal
Michael W. Mullowney, Eoghainin O. hAinmhire, Anam Shaikh, Xiaomei Wei, Urszula Tanouye, Bernard D. Santarsiero, Joanna E. Burdette, Brian T. Murphy
Article
Chemistry, Organic
Mark D. Aparece, Paul A. Vadola
Article
Chemistry, Multidisciplinary
Mark D. Aparece, Chenpeng Gao, Gabriel J. Lovinger, James P. Morken
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Biochemistry & Molecular Biology
Jorge C. Navarro-Munoz, Nelly Selem-Mojica, Michael W. Mullowney, Satria A. Kautsar, James H. Tryon, Elizabeth Parkinson, Emmanuel L. C. De Los Santos, Marley Yeong, Pablo Cruz-Morales, Sahar Abubucker, Arne Roeters, Wouter Lokhorst, Antonio Fernandez-Guerra, Luciana Teresa Dias Cappelini, Anthony W. Goering, Regan J. Thomson, William W. Metcalf, Neil L. Kelleher, Francisco Barona-Gomez, Marnix H. Medema
NATURE CHEMICAL BIOLOGY
(2020)
Article
Chemistry, Physical
Mark D. Aparece, Weipeng Hu, James P. Morken
Article
Multidisciplinary Sciences
Matthew R. Stutz, Nicholas P. Dylla, Steven D. Pearson, Paola Lecompte-Osorio, Ravi Nayak, Maryam Khalid, Emerald Adler, Jaye Boissiere, Huaiying Lin, William Leiter, Jessica Little, Amber Rose, David Moran, Michael W. Mullowney, Krysta S. Wolfe, Christopher Lehmann, Matthew Odenwald, Mark De la Cruz, Mihai Giurcanu, Anne S. Pohlman, Jesse B. Hall, Jean-Luc Chaubard, Anitha Sundararajan, Ashley Sidebottom, John P. Kress, Eric G. Pamer, Bhakti K. Patel
Summary: This study demonstrates that the composition of fecal microbiota and the concentrations of microbiota-derived metabolites can predict the trajectory of respiratory function and death in patients with severe SARS-Cov-2 infection, highlighting the importance of the gut-lung axis in the recovery from COVID-19.
NATURE COMMUNICATIONS
(2022)
Review
Biotechnology & Applied Microbiology
Michael W. Mullowney, Katherine R. Duncan, Somayah S. Elsayed, Neha Garg, Justin J. J. van der Hooft, Nathaniel I. Martin, David Meijer, Barbara R. Terlouw, Friederike Biermann, Kai Blin, Janani Durairaj, Marina Gorostiola Gonzalez, Eric J. N. Helfrich, Florian Huber, Stefan Leopold-Messer, Kohulan Rajan, Tristan de Rond, Jeffrey A. van Santen, Maria Sorokina, Marcy J. Balunas, Mehdi A. Beniddir, Doris A. van Bergeijk, Laura M. Carroll, Chase M. Clark, Djork-Arne Clevert, Chris A. Dejong, Chao Du, Scarlet Ferrinho, Francesca Grisoni, Albert Hofstetter, Willem Jespers, Olga V. Kalinina, Satria A. Kautsar, Hyunwoo Kim, Tiago F. Leao, Joleen Masschelein, Evan R. Rees, Raphael Reher, Daniel Reker, Philippe Schwaller, Marwin Segler, Michael A. Skinnider, Allison S. Walker, Egon L. Willighagen, Barbara Zdrazil, Nadine Ziemert, Rebecca J. M. Goss, Pierre Guyomard, Andrea Volkamer, William H. Gerwick, Hyun Uk Kim, Rolf Mueller, Gilles P. van Wezel, Gerard J. P. van Westen, Anna K. H. Hirsch, Roger G. Linington, Serina L. Robinson, Marnix H. Medema
Summary: The developments in computational omics technologies in combination with artificial intelligence approaches have opened up new possibilities for drug discovery. However, addressing key challenges such as high-quality datasets and algorithm validation is essential to realize the potential of these synergies.
NATURE REVIEWS DRUG DISCOVERY
(2023)
Meeting Abstract
Plant Sciences
M. W. Mullowney, E. O. HAinmhire, U. Tanouye, B. Wan, S. Cho, S. G. Franzblau, J. E. Burdette, P. Cuong, B. T. Murphy
Meeting Abstract
Plant Sciences
A. Shaikh, M. Mullowney, E. O'hainmhire, D. Colunga-Hernandez, J. Burdette, B. T. Murphy
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
