Article
Chemistry, Organic
Tony Z. Scott, Vinicius F. Armelin, Mohammad Movassaghi
Summary: This paper reports the first enantioselective total synthesis and stereochemical assignment of (-)-psychotridine. The highly convergent synthesis of the pentameric alkaloid was achieved through the application of diazene-directed assembly of enantiomerically enriched cyclotryptamines, allowing for detailed structural assignment. Notable highlights of the synthesis include the introduction of four quaternary stereocenters with complete stereochemical control in a single step via photoextrusion and metal-catalyzed C-H amination reactions under challenging conditions.
Article
Chemistry, Organic
Sourya Shankar Auddy, Sanu Saha, Rajib Kumar Goswami
Summary: Asymmetric total synthesis of an acetate analogue of the endophytic unstable secondary metabolite bipolamide A has been achieved for the first time adopting a convergent approach. The stereochemistry of the unassigned C-8 center of the naturally occurring unstable bipolamide A has been unambiguously established through our synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Fangzhi Han, Guangju Liu, Xiuhe Zhao, Shunshun Du, Yahui Ding, Quan Zhang, Huiting Deng, Liang Wang, Yue Chen
Summary: In this study, the total synthesis of rakicidin F was successfully achieved, allowing the determination of its stereogenic centers. The macrolactonization reaction of rakicidin precursor was also investigated, with steric hindrance near C16-OH identified as a possible cause for the unsuccessful results.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Franziska Gillsch, Haoxuan Zeng, Sofia Baer, Hedda Schrey, Rainer Schobert
Summary: This study successfully synthesized the metabolites of Ophiosphaerella korrae, Ophiofuranones A and B. The compounds were found to be non-toxic against tumor cells, fibroblasts, and various bacteria and fungi at relevant concentrations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tuan Minh Luong, Lisa Pilkington, David Barker
Summary: Lyoniresinol and its derivatives are natural compounds with various biological activities, which have been found in a wide range of plant species as well as in wines and spirits with gustatory effects. The first total asymmetric synthesis of these natural products and their deuterated analogues has been achieved, confirming their structure and stereochemistry. The synthesized compounds can serve as internal standards for improving lyoniresinol quantitation methods in the future.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Junyang Liu, Ying Chen, Hendrik Luesch, Tao Ye
Summary: The first asymmetric total synthesis and validation of the structural assignment of des-thiomethyllooekeyolide A (3) is described, which involves a Shiina macrolactonization and a late-stage pyran-hemiketal formation. The eight stereogenic centers of the C16-polyketide chain were installed by sequential aldol and crotylation reactions.
Article
Chemistry, Organic
Fangzhi Han, Guangju Liu, Chaofan Jin, Jinghan Wang, Jianwei Liu, Liang Wang, Yue Chen
Summary: The absolute configuration of rakicidin C was predicted using optical rotation data and compared with APD-cyclic depsipeptides, and then confirmed through total synthesis. The synthesis route involved 19 longest linear steps with an overall yield of 1.49%, determining the configuration of five chiral centers as 2R, 15R, 16R, 17S, and 19S.
Article
Chemistry, Organic
Chia-Chen Chang, Hau-Ming Jan, Chieh-Jen Tseng, Soumik Mondal, Andualem Bahiru Abera, Ming-Yen Hsieh, Tsai-Chen Yang, Sasikala Muthusamy, Sheng-Cih Huang, Chun-Hung Lin, Kwok-Kong Tony Mong
Summary: This study reports the isolation and stereochemical determination of the predominant native cholesteryl 6-O-phosphatidyl alpha- glucoside (CPG) from Helicobacter pylori. The authors used a combination of metabolic isolation and enzymatic degradation to obtain the native lactobacillic acid for stereochemical determination. The absolute stereochemistry of the acid was found to be 11R and 12S. Using this information, the authors achieved the total synthesis of predominant native CPG and other derivatives.
Article
Chemistry, Multidisciplinary
Christopher Y. Bemis, Chad N. Ungarean, Alexander S. Shved, Cooper S. Jamieson, Taehwan Hwang, Ken S. Lee, K. N. Houk, David Sarlah
Summary: This article describes a method for synthesizing sesquiterpene compounds and explains stereoselectivity through computational modeling studies, leading to stereochemical reassignments of the pycnidione subclass and providing new insights into the biosynthesis of these natural products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Chaoying Zheng, Tao Xie, Haibing He, Shuanhu Gao
Summary: A new approach was developed for the asymmetric total synthesis of (+)-PD-116740, involving a sequence of asymmetric dihydroxylation followed by oxidative cyclization. A new Cu salt was found to be the best oxidant for inducing the oxidative coupling and phenol oxidation, providing a valuable strategy for future pharmaceutical research.
Article
Chemistry, Organic
Gesa Hertrampf, Sandra Vojnovic, Jonas I. Mueller, Christian Merten, Jasmina Nikodinovic-Runic, Tobias A. M. Gulder
Summary: Myxocoumarin A from Stigmatella aurantiaca MYX-030 exhibits strong antifungal activity against agriculturally relevant pathogens. The total synthesis revealed its stereochemical configuration and demonstrated potent antibacterial activities against certain bacteria.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Takayuki Ohyoshi, Hidetada Iizumi, Shu Hosono, Hikaru Tano, Hideo Kigoshi
Summary: The total synthesis of aplysiasecosterols A and B has been accomplished. Key features of the synthesis include the Suzuki-Miyaura coupling of each AB-ring segment and common D-ring segment. This late-stage convergent synthesis, which has rarely been reported in secosteroid synthesis, can be adapted to many 9,11-secosteroids.
Article
Chemistry, Organic
Hongyuan Zhang, Haibing He, Shuanhu Gao
Summary: The asymmetric synthesis of the complex C-18 Cephalotaxus dinorditerpenoid cephanolide B was achieved for the first time using a remote hydroxyl group directed hydrogenation strategy and a sequence of modified transformations. The key hexahydrofluorenone core skeleton and selective reductions were crucial in achieving the target compound.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yinxin Liu, Jun Liu, Chuanfang Zhao, Yuguo Du
Summary: The stereoselective total synthesis of siladenoserinols A and D was achieved using carbohydrates as a chiral template. The key feature of this work is the construction of the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction, which could facilitate bioactivity investigation of siladenoserinols.
Article
Plant Sciences
Franziska Gillsch, Fredrick Mbui, Ursula Bilitewski, Rainer Schobert
Summary: The Penicillium metabolite thiocarboxylic A (1a) and three analogues were successfully synthesized in a modular synthetic route, which is of great significance for biological studies.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Immunology
Xiaozhen He, Ruiling Liu, Tingting Fan, Xiaowen Huang, Chunlei Wu, Wu Su, Ting Wang, Qingguo Ruan
JOURNAL OF IMMUNOLOGY
(2020)
Article
Chemistry, Medicinal
Chunlei Wu, Zhehong Cheng, Danyi Lu, Ke Liu, Yulian Cheng, Pengxin Wang, Yimin Zhou, Meiqing Li, Ximing Shao, Hongchang Li, Wu Su, Lijing Fang
Summary: Researchers discovered a simplified analogue of Coibamide A and designed two novel peptide-drug conjugates, with one showing better drug release in vitro and significant tumor growth suppression in mice-bearing human tumor xenografts, indicating great potential in cancer drug discovery.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Feng Qin, Cai Yi Wang, Donghwa Kim, Heng-Shan Wang, Yan-Kui Zhu, Sang Kook Lee, Gui-Yang Yao, Dong Liang
Summary: Nitidumpeptins A and B, two novel cyclic hexapeptides isolated from Zanthoxylum nitidum var. tomentosum, have unique structures and demonstrated synergistic antiproliferative activity in combination with gefitinib against gefitinib-resistant lung cancer cells. The total synthesis of these compounds confirmed their absolute configurations and further studies revealed the mechanism of action involved the suppression of YAP expression in the cancer cells.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Wenli Shi, Danyi Lu, Chunlei Wu, Meiqing Li, Zhihao Ding, Yanyan Li, Binghua Chen, Xian Lin, Wu Su, Ximing Shao, Zhihui Xia, Lijing Fang, Ke Liu, Hongchang Li
Summary: Coibamide A is a promising lead compound for cancer treatment due to its excellent tumor cell growth inhibitory profile and sub-nanomolar potency. It induces caspase-independent cell death and severe lysosome defects, blocking autophagosomelysosome fusion and leading to tumor cell death. These findings provide novel insights into the anti-cancer mechanism of action of Coibamide A.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Pengxin Wang, Yulian Cheng, Chunlei Wu, Yimin Zhou, Zhehong Cheng, Hongchang Li, Rui Wang, Wu Su, Lijing Fang
Summary: An efficient approach to preparing azobenzene functionalized peptides through late-stage modification of tyrosine-containing peptides using a dearomatization-rearomatization strategy was reported. This method demonstrates good chemoselectivity, site selectivity, and sensitivity to various peptides, enriching the postsynthetic modification toolbox of peptides and showing great potential for applications in medicinal chemistry and chemical biology.
Article
Biochemistry & Molecular Biology
Meiqing Li, Danyi Lu, Yulian Cheng, Chunlei Wu, Jianchao Zhang, Wenli Shi, Zhihao Ding, Yanyan Li, Binghua Cheng, Xian Lin, Ximing Shao, Hongchang Li, Lijing Fang, Ke Liu, Wu Su
Summary: The newly developed drug molecule PIP-Ht targets the Aurora A gene promoter and shows potent inhibitory effects on tumor cell growth and proliferation in vitro and in vivo, demonstrating potential as an effective candidate for cancer treatment.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Guiyang Yao, Caroline H. Knittel, Simone Kosol, Marius T. Wenz, Bettina G. Keller, Hendrik Gruss, Alexandra C. Braun, Christian Lutz, Torsten Hechler, Andreas Pahl, Roderich D. Sussmuth
Summary: The study presents an efficient method for constructing tryptathionine-cross-links in peptides between tryptophan and cysteine, which is essential for synthesizing alpha-amanitin and new amanitin analogues. It also provides a systematic compilation of structure-activity relations of amatoxins, showing potential for synthesizing structurally diverse amatoxins as future payloads for antibody-toxin conjugates in cancer therapy.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Nanoscience & Nanotechnology
Ximing Shao, Zhihao Ding, Wenhua Zhou, Yanyan Li, Zhibin Li, Haodong Cui, Xian Lin, Guoli Cao, Binghua Cheng, Haiyan Sun, Meiqing Li, Ke Liu, Danyi Lu, Shengyong Geng, Wenli Shi, Guofang Zhang, Qingle Song, Liang Chen, Guocheng Wang, Wu Su, Lintao Cai, Lijing Fang, David Tai Leong, Yang Li, Xue-Feng Yu, Hongchang Li
Summary: The study reveals a tumoricidal mechanism of black phosphorus nanomaterials where they directly affect the mitotic centrosome machinery by suppressing polo-like kinase 1, suggesting that nanomaterials can be applied in targeted cancer therapy with their intrinsic nano-bio properties.
NATURE NANOTECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Lauren M. Reid, Ileana Guzzetti, Tor Svensson, Anna-Carin Carlsson, Wu Su, Tomas Leek, Lena von Sydow, Werngard Czechtizky, Marija Miljak, Chandra Verma, Leonardo De Maria, Jonathan W. Essex
Summary: Understanding the conformational ensembles of intrinsically disordered proteins and peptides (IDPs) in different biological environments is crucial for understanding their mechanisms and functional roles, as well as potential treatments for diseases. This study investigates the structural landscape of the PLP peptide using molecular simulation and experimental validation, and identifies the CHARMM36m and REST2 protocol as suitable for studying environment-specific IDP conformations.
Article
Chemistry, Analytical
Frank Wesche, Leonardo De Maria, Tomas Leek, Frank Narjes, James Bird, Wu Su, Werngard Czechtizky
Summary: Inhalation of peptides offers the advantage of targeting lung tissue directly, but they are often quickly metabolized in the lungs. An assay workflow has been developed to study the half-life and metabolites of peptides in lung tissue, guiding early stage respiratory drug discovery projects through chemical modifications of peptide hits.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2022)
Article
Chemistry, Physical
Tillmann Utesch, Jana Staffa, Sagie Katz, Guiyang Yao, Jacek Kozuch, Peter Hildebrandt
Summary: The article investigates the effect of electrode potential on the transmembrane potential of lipid bilayers immobilized on gold electrodes. Experimental results and molecular dynamics simulations show good agreement, indicating the promising potential of this combined approach in studying potential-dependent processes at biomimetic interfaces.
JOURNAL OF PHYSICAL CHEMISTRY B
(2022)
Article
Multidisciplinary Sciences
Guiyang Yao, Simone Kosol, Marius T. Wenz, Elisabeth Irran, Bettina G. Keller, Oliver Trapp, Roderich D. Suessmuth
Summary: This article reports the use of the term "ansamer" to describe the isomers of the bicyclic octapeptide alpha-Amanitin. The researchers synthesized analogs of alpha-Amanitin and analyzed their isomers, proposing and describing the term "ansamer" for these isomers.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Analytical
Frank Wesche, Leonardo De Maria, Tomas Leek, Frank Narjes, James Bird, Wu Su, Werngard Czechtizky
Summary: Peptides and peptide drug conjugates are being used to treat pulmonary diseases, but they are susceptible to proteolytic cleavage. This study developed a high-throughput LC-HRMS protocol to determine enzymatic protease stability of peptides for inhaled administration. Testing of metabolic stability in lung fluid (BALF) was also conducted. The results showed significant differences compared to literature-derived estimates, indicating the need for experimental workflows to guide peptide optimization in drug discovery projects.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Pengxin Wang, Yulian Cheng, Chunlei Wu, Ruixiang Luo, Caibing Ma, Yimin Zhou, Zhilong Ma, Rui Wang, Wu Su, Lijing Fang
Summary: The dearomatization-rearomatization strategy modifies peptides/proteins through a specific chemical reaction, enriching the toolbox for conjugation and showing great potential for applications in medicinal chemistry and chemical biology.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Medicinal
Ke Liu, Rongfeng Zou, Wenqiang Cui, Meiqing Li, Xueying Wang, Junlin Dong, Hongchun Li, Hongpei Li, Peihui Wang, Ximing Shao, Wu Su, H. C. Stephen Chan, Hongchang Li, Shuguang Yuan
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2020)
