Stereochemical and Biosynthetic Rationalisation of the Tropolone Sesquiterpenoids DOI Creative Commons
Lei Li, Russell J. Cox

Journal of Fungi, Год журнала: 2022, Номер 8(9), С. 929 - 929

Опубликована: Авг. 31, 2022

This review summarises the known structures, biological activities, and biosynthetic pathways of tropolone sesquiterpenoid family fungal secondary metabolites. Synthesis this knowledge allows likely structural stereochemical misassignments to be revised shows how compounds can divided into three main classes based on stereochemistry key steps.

Язык: Английский

Experimental investigation on thermal management system with flame retardant flexible phase change material for retired battery module DOI
Yuming Li, Tingyu Wang, Xinxi Li

и другие.

Applied Energy, Год журнала: 2022, Номер 327, С. 120109 - 120109

Опубликована: Окт. 18, 2022

Язык: Английский

Процитировано

58

Deciphering chemical logic of fungal natural product biosynthesis through heterologous expression and genome mining DOI
Chen‐Yu Chiang, M. Ohashi, Yi Tang

и другие.

Natural Product Reports, Год журнала: 2022, Номер 40(1), С. 89 - 127

Опубликована: Сен. 20, 2022

Covering: 2010 to 2022Heterologous expression of natural product biosynthetic gene clusters (BGCs) has become a widely used tool for genome mining cryptic pathways, bottom-up investigation enzymes, and engineered biosynthesis new variants. In the field fungal products, heterologous complete pathway was first demonstrated in tenellin

Язык: Английский

Процитировано

49

Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide DOI Creative Commons
Stefan Wiesler, Goh Sennari, Mihai V. Popescu

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Май 15, 2024

Abstract Skeletal modifications enable elegant and rapid access to various derivatives of a compound that would otherwise be difficult prepare. They are therefore powerful tool, especially in the synthesis natural products or drug discovery, explore different improve properties candidate starting from common intermediate. Inspired by biosynthesis cephalotane products, we report here single-atom insertion into framework benzenoid subfamily, providing troponoid congeners — representing reverse proposed (i.e., contra-biosynthesis approach). Computational evaluation our designed transformation prompted us investigate Büchner–Curtius–Schlotterbeck reaction p -quinol methylether, which ultimately results harringtonolide two steps cephanolide A, had previously prepared. Additional computational studies reveal unconventional selectivity outcomes driven choice Lewis acid nucleophile, should inform further developments these types reactions.

Язык: Английский

Процитировано

11

Harnessing ortho-Quinone Methides in Natural Product Biosynthesis and Biocatalysis DOI
Trevor N. Purdy, Bradley S. Moore, April L. Lukowski

и другие.

Journal of Natural Products, Год журнала: 2022, Номер 85(3), С. 688 - 701

Опубликована: Фев. 2, 2022

The implementation of ortho-quinone methide (o-QM) intermediates in complex molecule assembly represents a remarkably efficient strategy designed by Nature and utilized synthetic chemists. o-QMs have been taken advantage biomimetic syntheses for decades, yet relatively few examples o-QM-generating enzymes natural product biosynthetic pathways reported. that discovered thus far exhibit tremendous potential biocatalytic applications, enabling the selective production desirable compounds are otherwise intractable or inherently difficult to achieve traditional methods. Characterization this machinery has shine light on new capable similar chemistry diverse substrates, expanding our knowledge Nature's catalytic repertoire. presently known include flavin-dependent oxidases, hetero-Diels–Alderases, S-adenosyl-l-methionine-dependent pericyclases, α-ketoglutarate-dependent nonheme iron enzymes. In review, we discuss their enzymatic mechanisms as biocatalysts constructing molecules such cannabinoids.

Язык: Английский

Процитировано

32

Tandem intermolecular [4 + 2] cycloadditions are catalysed by glycosylated enzymes for natural product biosynthesis DOI
Jia-Wang Liu,

Jiayan Lu,

Chen Zhang

и другие.

Nature Chemistry, Год журнала: 2023, Номер 15(8), С. 1083 - 1090

Опубликована: Июнь 26, 2023

Язык: Английский

Процитировано

21

Recent Advances in Chemistry and Antioxidant/Anticancer Biology of Monoterpene and Meroterpenoid Natural Product DOI Creative Commons
Benedict J. Barras,

Taotao Ling,

Fatima Rivas

и другие.

Molecules, Год журнала: 2024, Номер 29(1), С. 279 - 279

Опубликована: Янв. 4, 2024

Monoterpenes and meroterpenes are two large classes of isoprene-based molecules produced by terrestrial plants unicellular organisms as diverse secondary metabolites. The global rising incidence cancer has led to a renewed interest in natural products. These monoterpenes represent novel source molecular scaffolds that can serve medicinal chemistry platforms for the development potential preclinical leads. Furthermore, some these products either abundant, or their synthetic strategies scalable it will be indicated here, facilitating derivatization expand scope drug discovery. This review is collection representative updates (from 2016–2023) biologically active monoterpene meroterpenoid focuses on recent findings pharmacological bioactive compounds well newly developed employed access them. Particular emphasis placed anticancer antioxidant order raise knowledge further investigations into anti-cancer therapeutics. mounting experimental evidence from various research groups across globe regarding use at pre-clinical levels, renders them fast-track area worth attention.

Язык: Английский

Процитировано

9

Engineered and total biosynthesis of fungal specialized metabolites DOI
Russell J. Cox

Nature Reviews Chemistry, Год журнала: 2024, Номер 8(1), С. 61 - 78

Опубликована: Янв. 3, 2024

Язык: Английский

Процитировано

8

Synthesis of Polysubstituted Enamides by Hydrogen Atom Transfer Alkene Isomerization Using Dual Cobalt/Photoredox Catalysis DOI

Yusuke Seino,

Yuto Yamaguchi,

Akihiko Suzuki

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(37)

Опубликована: Апрель 19, 2023

M-HAT isomerization is a highly reliable method to access thermodynamically stable alkenes with high functional group tolerance. However, synthesis of heteroatom-substituted by reaction still underdeveloped. Herein, we report an enamide using via combination cobalt and photoredox catalysis. This tolerates variety groups including haloarenes, heteroarenes, free hydroxy groups, non-protected indoles, drug derivatives. Furthermore, this can isomerize styrene derivatives in good yield E/Z selectivity.

Язык: Английский

Процитировано

12

Late-Stage “Benzenoid-to-Troponoid” Skeletal Modification of the Cephalotanes: Total Synthesis of Harringtonolide and Computational Analysis DOI Creative Commons
Stefan Wiesler, Goh Sennari, Mihai V. Popescu

и другие.

Опубликована: Фев. 6, 2024

Inspired by the biosynthesis of cephalotane natural products, we envisioned that a “single-atom insertion” into framework benzenoid subfamily would provide access to troponoid congeners — representing reverse proposed (i.e., “contra-biosynthesis” approach). Computational evaluation our designed transformation prompted us investigate Büchner–Curtius–Schlotterbeck reaction p-quinol methylether, which ultimately resulted in synthesis harringtonolide two steps from cephanolide A, had previously prepared. Additional computational studies revealed unconventional selectivity outcomes were driven choice Lewis acid and nucleophile, should inform further developments these types reactions.

Язык: Английский

Процитировано

5

Carbocycloaddition strategies for troponoid synthesis DOI Creative Commons
Ryan P. Murelli, Alex J. Berkowitz, Daniel W. Zuschlag

и другие.

Tetrahedron, Год журнала: 2022, Номер 130, С. 133175 - 133175

Опубликована: Дек. 1, 2022

Язык: Английский

Процитировано

19