Article
Chemistry, Organic
Rainer Koch, Martin Podszus, Andreas Opitz
Summary: The study investigates the Fischer indole synthesis of ketone 1 with phenylhydrazine using DFT methods. A detailed reaction mechanism is proposed, including various plausible rearrangement pathways. It is found that the cis-/trans-stereochemistry of substrate 1 leads to different pathways and products, and the influence of hydrazine protonation on the mechanism is also considered.
Article
Multidisciplinary Sciences
Haoyu Tang, Min-Hao Wu, Hsiao-Yu Lin, Meng-Ru Han, Yueh-Hua Tu, Zhi-Jie Yang, Tun-Cheng Chien, Nei-Li Chan, Wei-chen Chang
Summary: This study reports the structure and catalytic mechanism of deoxypodophyllotoxin synthase, and finds that the cyclization reaction likely proceeds through hydrogen atom abstraction, ring closure, and rearomatization. This finding provides guidance for the synthesis of deoxypodophyllotoxin analogs.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2022)
Article
Chemistry, Medicinal
Wei Liu, Liang Ma, Liping Zhang, Yuchan Chen, Qingbo Zhang, Haibo Zhang, Weimin Zhang, Changsheng Zhang, Wenjun Zhang
Summary: Two new phenylhydrazone derivatives and one new alkaloid, along with three known compounds, were isolated from Streptomyces sp. SCSIO 40020 obtained from the Pearl River Estuary sediment. Their structures and absolute configurations were determined using NMR, mass spectroscopy and X-ray crystallography. Compound 1 showed weak cytotoxicity in three cancer cell lines. Analysis of the putative biosynthetic gene cluster suggested the involvement of a Japp-Klingemann coupling reaction in the synthesis of compounds 1 and 2.
Article
Chemistry, Physical
Jiachun Chai, Robert Pestman, Wei Chen, Noortje Donkervoet, A. Iulian Dugulan, Zhuowu Men, Peng Wang, Emiel J. M. Hensen
Summary: The kinetics of the transformation of metallic Fe to the active Fe carbide phase at the start of the Fischer-Tropsch (FT) reaction were studied. The diffusion rates of C atoms going in or out of the lattice were determined using C-13-labeled synthesis gas. It was found that in the initial stages, C diffused rapidly into the lattice, and the FT reaction started during this period. When reaching steady state, the diffusion rates of C in and out of the lattice converged, and the FT reaction continued via two parallel reaction mechanisms. The outer layers of the Fe carbide were involved in hydrocarbon formation via a slow reaction, contributing to around 10% of the total activity.
Article
Chemistry, Physical
Tzu-Yu Chen, Ziyang Zheng, Xuan Zhang, Jinfeng Chen, Lide Cha, Yijie Tang, Yisong Guo, Jiahai Zhou, Binju Wang, Hung-wen Liu, Wei-chen Chang
Summary: Researchers have investigated the catalytic mechanism of several Fe/2OG enzymes capable of catalyzing isocyanide formation, and found that the reaction likely involves two steps: the formation of an imine intermediate and decarboxylation-assisted desaturation.
Article
Biochemistry & Molecular Biology
Bolin Du, Xiaoxia Liu, Xin Luan, Weidong Zhang, Chunlin Zhuang
Summary: Two series of 4-methoxyphenyl derivatives of FC116 were developed, among which FC11619 exhibited potent in vitro cytotoxicity against HCT-116 colorectal cancer cells in the low nanomolar range. This compound induced G2/M phase arrest, produced excess reactive oxygen species, and targeted tubulin in CRC cells. In vivo, FC11619 significantly suppressed tumor growth, achieving superior inhibition rates compared to Taxol. Additionally, FC11619 showed better in vivo tolerance and no major organ-related toxicity, making it a promising lead compound for further drug development in colorectal cancer therapy.
BIOORGANIC CHEMISTRY
(2023)
Review
Biology
Vonny Salim, Sara-Alexis Jarecki, Marshall Vick, Ryan Miller
Summary: Monoterpene indole alkaloids (MIAs) are a diverse family of over 3000 plant natural products with a wide range of medical applications. However, their low abundance in natural sources and complex synthesis processes hinder further utilization. Metabolic engineering of MIAs biosynthesis in heterologous hosts is an attractive approach to increase yield and expand chemical diversity. This review discusses recent advances, strategies, current issues, and future developments in manufacturing MIAs through synthetic biology approaches.
Article
Chemistry, Organic
Ryoma Shimazumi, Kosuke Morita, Tomoki Yoshida, Kosuke Yasui, Mamoru Tobisu
Summary: This nickel-catalyzed cross-coupling reaction allows for the selective monosubstitution of one methoxy group in buflavine, leading to the formation of various derivatives by introducing different groups into the molecule.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Physical
Jiachun Chai, Robert Pestman, Fu-Kuo Chiang, Zhuowu Men, Peng Wang, Emiel J. M. Hensen
Summary: The deactivation of Fe-carbide catalysts in the Fischer-Tropsch reaction is caused by carbon deposition. Carbon deposition affects the product distribution by inhibiting C-C coupling and decreasing the formation of longer hydrocarbons. Increasing the H2/CO ratio or total pressure can suppress carbon deposition.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Simon X. Lin, Jonathan Sperry
Summary: The synthesis of lysiformine, a bisindole alkaloid, was described. The heterocyclic framework of the natural product was assembled using iterative Suzuki coupling and reductive alkylation reactions starting from a pyridine derived from kojic acid. NMR spectroscopic analysis confirmed that the synthetic sample matched well with the natural product, highlighting the rarity of a marine natural product containing a 3-hydroxypyridine.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Nadezhda S. Demina, Polina E. Bayankina, Roman A. Irgashev, Nikita A. Kazin, Gennady L. Rusinov
Summary: A series of N,S-heterohexacenes were efficiently synthesized in three steps from available starting materials, utilizing various reagents and methods, ultimately yielding the desired products.
Article
Chemistry, Multidisciplinary
Hatem M. Altass, Moataz Morad, Abdelrahman S. Khder, Mohamed Raafat, Reem Alsantali, Menna A. Khder, Reda S. Salama, M. Shaheer Malik, Ziad Moussa, Mohammed A. S. Abourehab, Saleh A. Ahmed
Summary: Solid acidic cerium tungstate catalysts with different molar ratios of cerium and tungstate were prepared using direct solvothermal methodology. The catalysts' structure and properties were studied and confirmed through various characterization techniques. The study showed that the catalysts' structure and properties were influenced by the molar ratio of tungstate, and they exhibited excellent acidic properties. Furthermore, the acidic properties of the catalysts were successfully utilized for the synthesis of indole derivatives, and the catalysts demonstrated high efficiency and reusability through multiple cycles.
ARABIAN JOURNAL OF CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Marco Kruppa, Thomas J. J. Mueller
Summary: Marine natural products are highly diverse and possess a wide range of biological activities. The (aza)indole alkaloids variolin B (1), meridianins (2), and their synthetic hybrids meriolins (3) have attracted significant interest due to their potent kinase inhibitory activities. This review provides an overview of the synthetic strategies employed to access these naturally occurring alkaloids and their semisynthetic derivatives.
Article
Engineering, Environmental
Shi Liu, Zhiwei Ge, Mingming Du, Liejin Guo
Summary: This paper investigates the gasification characteristics and nitrogen distribution in the supercritical water partial oxidation (SCWPO) process of indole. The results reveal the influencing factors on gas product formation and propose an SCWPO mechanism for indole.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Jianfeng Li, Xiaoting Wang, Rong-Ping Zhang, Lei Chen
Summary: Scalable syntheses of piceatannol-3'-O-beta-d-glucopyranoside and its 4'-methoxy counterpart were achieved using a route that includes early implemented Fischer-like glycosylation reaction, regioselective iodination of phenolic glycoside under strongly acidic conditions, highly telescoped route to access the styrene derivative, and key Mizoroki-Heck reaction for high overall yield of desired products.
SYNTHESIS-STUTTGART
(2022)
