Article
Chemistry, Multidisciplinary
Hong-Gang Cheng, Zhenjie Yang, Ruiming Chen, Liming Cao, Wen-Yan Tong, Qiang Wei, Qingqing Wang, Chenggui Wu, Shuanglin Qu, Qianghui Zhou
Summary: A concise total synthesis of (-)-berkelic acid is reported in eight linear steps, featuring a Catellani reaction/oxa-Michael cascade, a one-pot deprotection/spiroacetalization operation, and a late-stage Ni-catalyzed reductive coupling. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process, supported by DFT calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Datendra Nath Tripathi, Saravanakumar Rajendran
Summary: A concise and straightforward synthetic route to produce DHCUR and its analogs in excellent yields is reported. The developed protocol provides easy access for therapeutic study of bioactive natural products, 1,7-diarylheptanoids and DHCUR.
Article
Chemistry, Multidisciplinary
Soojun Park, Jiwoo Lee, Jae Hyun Kim, Yeji Jeong, Seokwoo Lee, Su Won Lee, Sanghee Kim
Summary: A concise total synthesis of salinosporamides and cinnabaramides was achieved through the combined use of memory of chirality and dynamic kinetic resolution principles, involving aldol reactions and hydrolysis reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Atsushi Nakayama, Tenta Nakamura, Toshihiro Zaima, Saho Fujimoto, Sangita Karanjit, Kosuke Namba
Summary: The concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was achieved through a one-pot construction of a pentacyclic skeleton. This strategy, controlled by the stereocenter at the C14 position, can be used to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Materials Science, Multidisciplinary
Yi Fang, Jialai Wang, Liang Wang, Xin Qian, Xiaodong Wang, Wenyu Liao, Peiyuan Chen, Hongyan Ma
Summary: In this study, tannic acid (TA), a bio-inspired, plant-derived polyphenol, was found to enhance the compressive strength of concretes as a renewable admixture. The experimental results showed that TA could retard the hydration of tricalcium silicate (alite) and alter the hydration products by forming complexes with calcium ions. Furthermore, TA reduced the mean chain length of calcium silicate hydrate (C-S-H), eliminated pores with a size near 30 nm, and resulted in higher elastic modulus of the produced CASAH and higher compressive strength of the produced concrete.
MATERIALS & DESIGN
(2023)
Article
Chemistry, Organic
Jian Li, Hans Renata
Summary: A novel chemoenzymatic approach was developed for the synthesis of fasamycin A, a halogenated naphthacenoid with activities against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecalis. The synthesis involved combining two fragments through a Sammes annulation to form a dimethylnaphthacenone system, followed by enzymatic halogenation to introduce the necessary chlorine substituent at a later stage.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Yun-Fei Cheng, Hui-Jing Li, Xiao-Bo Wang, Yan-Chao Wu
Summary: A facile synthesis method has been developed for the marine natural product Smenodiol, achieving a high overall yield of 23.2% within 8 steps from easily available starting materials. This method involves a TMSOTf-mediated Friedel-Crafts reaction with a methyl ester in the aryl as the key step, enabling a concise synthesis of the marine natural product (-)-Pelorol.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Organic
Zhenjie Yang, Hong-Gang Cheng, Ruiming Chen, Liming Cao, Qiang Wei, Qingqing Wang, Qianghui Zhou
Summary: We report an eight-step asymmetric synthesis of (-)-berkelic acid. This method involves a sequential Catellani-type reaction/oxa-Michael addition for synthesizing the isochroman framework, a one-pot, acid-catalyzed deprotection/spiroacetalization process for constructing a tetracyclic core intermediate, and a late-stage Ni-catalyzed reductive coupling reaction for installing the side chain. Notably, four new stereocenters are created with high stereocontrol from a single existing chiral center during the deprotection/spiroacetalization process.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Balasaheb R. Borade, Ravindar Kontham
Summary: A chiral-pool protecting-group-free five-step total synthesis of tetranorsesquiterpenoide (+)-lanceolactone A and its stereoisomers was achieved using linalool as building blocks. The key steps in this synthesis include regioselective ozonolysis, cycloisomerization-induced construction of furan, and dye-sensitized photo-oxidation. The absolute configuration of natural lanceolactone A was determined using electronic circular dichroism (ECD) and optical rotation data. The study also extended the application of Feringa and Gawronski's CD correlation method.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Jiyong Zheng, Haiping Gao, Guanglong Zhang, Zhiyong Sun, Jinwei Zhang, Li Wang, Cunguo Lin
Summary: Researchers have created a marine antifouling compound, OHBA, inspired by ceramide and paeonol molecules. OHBA has been shown to have broad-spectrum antifouling properties, inhibiting the growth of various marine fouling organisms. Additionally, OHBA is highly biodegradable, making it a more environmentally-friendly alternative.
NATURAL PRODUCT RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Emmanuel Cigan, Jakob Pletz, Sarah A. Berger, Bettina Hierzberger, Michael Grilec-Zlamal, Alexander Steiner, Isabel Oroz-Guinea, Wolfgang Kroutil
Summary: This study demonstrates an efficient access to the morphinan scaffold using a combination of organic synthesis and enzymatic reactions. The synthesis of a medicinally important compound class, promorphinans, was achieved by minimizing protecting group techniques and utilizing biocatalysis.
Article
Chemistry, Multidisciplinary
Emmanuel Cigan, Jakob Pletz, Sarah A. Berger, Bettina Hierzberger, Michael Grilec-Zlamal, Alexander Steiner, Isabel Oroz-Guinea, Wolfgang Kroutil
Summary: A biomimetic chemo-enzymatic strategy was demonstrated to efficiently synthesize the natural promorphinan intermediate (+)-salutaridine. This was achieved by combining organic synthesis and enzymatic transformations, resulting in high yields and enantioselectivities. This approach provides an unprecedented access to the medicinally important compound class of promorphinans.
Article
Biochemistry & Molecular Biology
Chunngai Hui, Andrey P. Antonchick
Summary: A concise synthesis of piperarborenine B is reported, which involves multiple steps including organocatalytic electrophilic amination and stereospecific oxidative ring contraction. The synthesis was achieved without the use of transition metals, directing groups or protecting groups, providing a novel strategy for the preparation of a non-symmetrical cyclobutane core.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuanzhi Li, Mengqian Zhu, Liang Xu
Summary: A concise biogenetically inspired formal synthesis of camptothecin has been developed, utilizing key reactions such as Pictet-Spengler reaction, intramolecular oxa-Diels-Alder reaction, and Winterfeldt biomimetic oxidation without the use of protecting groups.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lei Li, Weida Liang, Mario E. Rivera, Ye-Cheng Wang, Mingji Dai
Summary: A concise synthesis of (-)-GA18 methyl ester from commercially available and cheap andrographolide is reported. The synthesis involves intramolecular ene reaction, oxidative cleavage and aldol condensation, photochemical cycloaddition, and skeletal rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Samuel D. Offei, Hadi D. Arman, Francis K. Yoshimoto
Article
Plant Sciences
Kaitlyn Varela, Hadi D. Arman, Francis K. Yoshimoto
JOURNAL OF NATURAL PRODUCTS
(2020)
Article
Biochemistry & Molecular Biology
Ephrahime S. Traore, Jiasong Li, Tapiwa Chiura, Jiafeng Geng, Ankita J. Sachla, Francis Yoshimoto, Zehava Eichenbaum, Ian Davis, Piotr J. Mak, Aimin Liu
Summary: The HupZ protein binds heme through its His(6)-tag, leading to heme-induced higher-order oligomeric structure and heme stacking. The results do not support the classification of HupZ as a heme oxygenase, as slow heme binding and weak heme degradation activity are associated with the His(6)-tag.
Article
Biochemistry & Molecular Biology
Francis K. Yoshimoto
Summary: The global pandemic in 2020 was caused by the virus SARS CoV-2, with discussions on the chemistry of its various nonstructural proteins and the significance of variant strains. The emerging strains like D614G, 501Y.V1, and 501Y.V2 show structural changes that increase infectivity, emphasizing the need for continued efforts in researching and understanding this rapidly evolving virus.
Article
Plant Sciences
Kaitlyn Varela, Hadi D. Arman, Francis K. Yoshimoto
Summary: Artemisinin, a plant natural product used for treating malaria, has its antiparasitic properties attributed to the endoperoxide bridge. Study on isotopologues of dihydroartemisinic acid and UV-C radiation revealed new insights into the mechanism of endoperoxide formation, aiding in understanding the biosynthesis of artemisinin.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Biochemistry & Molecular Biology
Francis K. Yoshimoto, Lawrence J. Berliner
Summary: COVID-19, caused by SARS CoV-2, continues to puzzle the world, with new mutant strains evolving to be more infectious. The special issue on SARS CoV-2 proteins in the Protein Journal has been introduced in this update.
Article
Biochemistry & Molecular Biology
Eunhee Chung, Samuel D. Offei, U-Ter Aondo Jia, Juan Estevez, Yessenia Perez, Hadi D. Arman, Francis K. Yoshimoto
Summary: Researchers have discovered that mice lacking the gene for P450 8B1 show resistance to weight gain and improved glucose tolerance when fed a high-fat diet. This finding suggests that inhibiting P450 8B1 could be a potential treatment for obesity-associated metabolic disorders.
Article
Plant Sciences
Kaitlyn Varela, Hafij Al Mahmud, Hadi D. Arman, Luis R. Martinez, Catherine A. Wakeman, Francis K. Yoshimoto
Summary: This study investigates the importance of the monoalkene functional group in initiating the endoperoxide-forming cascade reaction to yield artemisinin from DHAA. The study also demonstrates the application of spontaneous aromatization process in other natural products. The synthesized compounds in this study show inhibitory activity against bacterial and fungal pathogens.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Jinghan Liu, Samuel D. Offei, Francis K. Yoshimoto, Emily E. Scott
Summary: The human oxysterol 12 alpha-hydroxylase cytochrome P450 8B1 (CYP8B1) is an important drug target for type 2 diabetes and nonalcoholic fatty liver disease. However, selective inhibitors for CYP8B1 are still lacking. In this study, steroidal substratemimicking compounds were designed with a pyridine ring appended to the site of metabolism for inhibitory activity against CYP8B1. While the intended interaction between the pyridine nitrogen and the heme iron of CYP8B1 did not occur, the cocrystallization of a pyridine-containing compound with a similar steroid backbone to the endogenous substrate revealed a ligand bound in a channel leading to the active site. Further analysis suggests that tryptophan 281 may restrict the binding of potential inhibitors with this design, as mutation of this amino acid allowed the compounds to coordinate the heme iron as intended. These findings provide insight for the design of next-generation CYP8B1 inhibitors.
JOURNAL OF BIOLOGICAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hadi D. Arman, Tu M. Ho, Kaitlyn Varela, Cynthia S. Veliz, Richard B. Zanni, Armando Rodriguez, Zhiwei Wang, Francis K. Yoshimoto
Summary: This study describes a semester-long biochemistry laboratory course that provided undergraduate students with meaningful research experiences. The course focused on exploring the use of cytochrome P450 enzymes in metabolizing artemisinin. Students were introduced to both computational and experimental techniques, and the semester culminated with the use of a web-based program and virtual reality headset. The course serves as a valuable model for future biochemistry laboratory courses taught in the course-based undergraduate research experiences (CUREs) format.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Plant Sciences
Kaitlyn Varela, Hadi D. Arman, Mitchel S. Berger, Valerie M. Sponsel, Chin-Hsing Annie Lin, Francis K. Yoshimoto
Summary: Artemisia annua produces artemisinin, a compound used to treat malaria. A. annua extracts contain other bioactive compounds and have potential therapeutic effects on cancer and COVID-19.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Biochemistry & Molecular Biology
Francis K. Yoshimoto, Samantha Q. Guerrero, Tu M. Ho, Hadi D. Arman
Summary: In this study, 6 beta-hydroxytestosterone was synthesized through oxidation reaction and used to synthesize 6 beta-hydroxyandrostenedione as a standard substance. The synthesis route and catalytic activity of P450 3A4 were successfully investigated.
Article
Biochemistry & Molecular Biology
Tu M. Ho, Hadi D. Arman, Francis K. Yoshimoto
Summary: Low concentrations of hyocholic acid in human serum have been linked to diabetes. Synthesis of hyocholic acid from chenodeoxycholic acid was reported, and its biochemical properties were explored. Cleavage of the C6-C7 bond in hyocholic acid using NaIO4 was used to distinguish it from cholic acid.
Article
Chemistry, Organic
Samuel D. Offei, Hadi D. Arman, Francis K. Yoshimoto
Summary: Menarandroside A, isolated from Cynanchum menarandrense, increased the secretion of GLP-1, which is beneficial for treating type 2 diabetes. The synthesis of menarandroside A from DHEA was disclosed, involving key steps of Wittig reaction and stereoselective reduction. In addition, an oxidation method using TPAP and NMO was discovered.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Francis K. Yoshimoto
