Article
Chemistry, Physical
Wakana Ishioka, Ken-ichi Nihei
Summary: A series of resorcinol alkyl glucosides were synthesized and evaluated for their tyrosinase inhibitory activity, showing that the activity was enhanced with the increasing length of the alkyl chain. The study also indicated that the presence of sugar and hydroxy groups adjacent to the resorcinol ring interfered with its functioning.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Xiaoqian Li, Zhi Ma, Rongkun Liu, Mattan Hurevich, You Yang
Summary: A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. Multiple oNBC groups in the 2-deoxy-glycosides can be completely cleaved by irradiation at 365 nm, resulting in the desired 2-deoxy-glycosides in an efficient manner. Oligosaccharides with three to six oNBC groups are effectively achieved based on this PPG-mediated glycosidation approach.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Weidong Shang, Rong Shi, Dawen Niu
Summary: C-glycosides are important natural products and potential medicinal candidates. Nickel-catalyzed C-glycosylation reactions provide a promising strategy for their synthesis. Achieving stereoselective synthesis of alpha- and beta-C-glycosides has been a challenge, but recent developments in nickel-mediated strategies have addressed this problem. This review summarizes the advancements in diastereoselective C-glycosylation reactions and discusses the mechanistic understandings of these methods.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Lei Sun, Bo Lu, Yandan Liu, Qian Wang, Gao Li, Longxuan Zhao, Chunhui Zhao
Summary: Quercetin derivatives were synthesized selectively through different reactions and their structures were characterized. The antioxidant capacity of the synthesized compounds was significant, with Qr-12 showing the strongest activity.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Shuang An, Quanquan Wang, Wanjun Zhu, Qikai Sun, Gang He, Gong Chen
Summary: A new protocol for glycosylation using glycosyl chloride donors under palladium-catalyzed conditions has been developed. This method is operationally simple, robust, and enables efficient synthesis of various glycosides, including N-ribonucleoside analogs.
Article
Chemistry, Multidisciplinary
Quanquan Wang, Wanjun Zhu, Qikai Sun, Gang He, Gong Chen
Summary: A novel Pd-catalyzed ortho-directed C-H glycosylation reaction using N-linked bidentate auxiliaries has been developed for efficient synthesis of C-aryl glycosides with high yield and selectivity. This method allows for installation of a wide range of pyranose and furanose moieties on various substrates and facile installation and removal of the auxiliaries under mild conditions.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Divya Rajendran, Jebasingh Bhagavathsingh
Summary: The study presents a convenient synthesis of O-galactosylation by reacting Boc-activated diphenols with alpha-bromoacetogalactose. The protection of amine and diphenolic hydroxyl group enhances the formation of galactosylated products in two steps. The yields of beta-isomer L-DOPA glycoside reach 72-84% through Boc-activation of hydroxyl group in diphenols.
Article
Chemistry, Multidisciplinary
Kazuki Kurahayashi, Kengo Hanaya, Takeshi Sugai, Go Hirai, Shuhei Higashibayashi
Summary: Metabolically stable C-glycosides play a crucial role in bioactive natural products, therapeutic agents, and biological probes. The development of synthetic methods for connecting glycosides and aglycons with strict stereocontrol is essential. In this study, a copper-catalyzed one-step borylation of glycosyl bromides to glycosyl boronates and a palladium-catalyzed cross-coupling of β-glycosyl borates with aryl bromides were successfully achieved, resulting in the synthesis of aryl β-C-glycosides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Yang-Fan Guo, Tao Luo, Guang-Jing Feng, Chun-Yang Liu, Hai Dong
Summary: An improved method for efficiently synthesizing 2-OH thioaryl glycosides from per-protected glycals was developed. The method involved the oxidation of glycals with oxone to prepare 1,2-anhydro sugars, followed by reaction with NaBH4 and aryl disulfides. This method was also used in a one-pot reaction to synthesize glycosyl donors with both armed and NGP effects.
Article
Chemistry, Multidisciplinary
Shiyang Xu, Wei Zhang, Caiyi Li, Yanjing Li, Hongxin Zeng, Yingwei Wang, Yang Zhang, Dawen Niu
Summary: We present a method for generating glycosyl radicals under highly acidic conditions. This method utilizes glycosyl sulfinates as radical precursors, which are stable solids and can be easily prepared from commercial starting materials. The method allows for direct installation of glycosyl units onto pyridine rings through the Minisci reaction. We showcase the utility of the method in the late-stage modification of complex drug molecules, including camptothecin. Experimental studies provide insight into the reaction mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Eric M. Miller, Maciej A. Walczak
Summary: This study presents stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters, exhibiting high anomeric selectivities for 2-deoxysugars and showing a broad substrate scope, including disaccharides and trifluoroborates with free hydroxyl groups. This new class of carbohydrate reagents adds to the palette of anomeric nucleophile reagents suitable for efficient installation of C-C bonds.
Article
Biochemistry & Molecular Biology
Sonali Priyadarshini Parida, Tapaswini Das, Mohammed Ansar Ahemad, Tapaswini Pati, Seetaram Mohapatra, Sabita Nayak
Summary: In recent years, significant efforts have been devoted to the construction of C-glycosidic linkages in carbohydrate compounds, as they serve as important building blocks for many alkaloids and pharmaceutically active drug molecules. This review summarizes the recent developments in diverse synthesis of C-glycoside core between 2019 and 2022, with a focus on different catalytic strategies including transition-metal and metal-free approaches. The transition-metal catalyzed C-glycosylations are categorized into four sub classes: metal-based C-H activation, cross-coupling reactions, glycosyl radical intermediate-based processes, and others.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Applied
Kameshwar Prasad, Ananay Sharma, Soumyaranjan Pati, Marc Taillefer, Florian Jaroschik, Srinivas Hotha
Summary: We report metal free conditions for the activation of alkynyl glycosyl carbonate donors using I-2/TMSOTf in stoichiometric quantities. The extrusion product was characterized as vinylidene iodide by single crystal X-ray analysis. The reaction conditions were suitable for the synthesis of various glycosides, purine/pyrimidine nucleosides, and a pentasaccharide repeating unit of Klebsiella pneumoniae (O-3 antigen).
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Carla Obradors, Benjamin Mitschke, Miles H. Aukland, Markus Leutzsch, Oleg Grossmann, Sebastian Brunen, Sebastian A. Schwengers, Benjamin List
Summary: Since early 2020, scientists have been striving to find effective solutions to combat SARS-CoV-2, focusing on developing reliable vaccines and repurposing drugs. However, the current synthetic routes for Remdesivir, the most widely used therapeutic during the early stages of infection, face challenges in cost-effective supply to patients. In this study, researchers have developed a straightforward method for adding (hetero)arenes to unprotected sugars, significantly expediting the synthesis of Remdesivir precursor GS-441524.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Thomas Hansen, Tim P. Ofman, Joey G. C. Vlaming, Ivan A. Gagarinov, Jessey van Beek, Tessa A. Gote, Jacoba M. Tichem, Gijs Ruijgrok, Herman S. Overkleeft, Dmitri V. Filippov, Gijsbert A. van der Marel, Jeroen D. C. Codee
Summary: By systematically studying the reactivity-stereoselectivity relationships of caryophyllose donor and acceptor glycosides, using experimental and computational techniques, we were able to design carbohydrate building blocks with the necessary properties to assemble mycobacterial lipooligosaccharide fragments of M. marinum.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Analytical
Pooja Rawat, Parul Nain, Shaveta Sharma, Parshant Kumar Sharma, Vidhu Malik, Sudip Majumder, Ved Prakash Verma, Varun Rawat, Jong Soo Rhyee
Summary: Carbon quantum dots (CQDs) are promising carbonaceous nanomaterials with unique properties and wide applications. They are known for their excellent solubility and luminescence, and can be efficiently and economically prepared through sustainable chemical strategies. Recent advances have been made in the photoluminescence applications of CQDs in chemical and biological fields.
Article
Chemistry, Inorganic & Nuclear
Dilip Kumar Jangid, Saptarshi G. Dastider, Rathindranath Biswas, Samreet Khirid, Sangeeta Meena, Pankaj Kumar, Subash C. Sahoo, Ved Prakash Verma, Ravindra D. Makde, Ashwani Kumar, Ravindra Jangir, Krishnakanta Mondal, Krishna Kanta Haldar, Rajendra S. Dhayal
Summary: A series of heterometallic clusters were synthesized and characterized, showing potential in water splitting activity, with longer carbon chain length and alkoxy group length leading to decreased catalytic performance. Even after stability tests and cycles, cluster 1 exhibited good catalytic durability with only a slight increase in overpotential. Density functional theory analysis supported experimental results.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Varun Rawat, Arkadi Vigalok, Anshu Kumar Sinha, Garima Sachdeva, Chandra Mohan Srivastava, Gyandshwar K. Rao, Arun Kumar, Mandeep Singh, Komal Rathi, Ved Prakash Verma, Bhupender Yadav, Amit Kumar Pandey, Monika Vats
Summary: The synthesis and characterization of a new octahedral Zr(IV) complex of oxygen-depleted N,O-type calixarene ligand comprising two distal-functionalized pyrazole rings have been reported. The cone shape and structure of the prepared complex were confirmed univocally by single-crystal X-ray diffraction and NMR studies. This complex has been utilized as an efficient catalyst for the synthesis of Biginelli adducts, bis(indolyl)methanes, and coumarins. In addition, a ferrocene-appended bis(indolyl)methane prepared using this catalyst showed promising anticancer activity against the A-172 cell line.
Article
Chemistry, Physical
Bhawna Rani, Neelam Sharma, Rahul Shrivastava, Arunava Agarwala, Ved Praksah Verma
Summary: A styryl-BODIPY based receptor (SBT) has been synthesized as a colorimetric chemosensor for selective sensing of CN- and Cu2+ ions. The receptor exhibited notable optical color changes in the presence of aqueous solutions of CN- and Cu2+ ions respectively. It showed a linear shift in absorption peak for sensing CN- ions and selective sensing of Cu2+ ions over other competitive cations with detection limits lower than the recommended concentration of Cu2+ in drinking water.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Yasmeen Bakhatan, Israel Alshanski, Chieh-Kai Chan, Wei-Chih Lo, Po-Wei Lu, Pin-Hsuan Liao, Cheng-Chung Wang, Mattan Hurevich
Summary: Solid-phase synthesis is the main method for preparing biological oligomers. Accelerated solid-phase synthesis is crucial for chemical biology but is not easy for oligosaccharide synthesis. High shear stirring is a new approach to accelerate solid-phase synthesis by improving mixing efficiency. In this study, we used high shear mixing to perform diffusion-dependent glycosylation and completed full glycosylation cycles in minutes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Chun-Hong Yeh, Ya-Jou Chang, Tsung-Juin Lin, Cheng-Chung Wang
Summary: This article presents a total synthesis of a C. jejuni NCTC11168 capsular polysaccharide repeating unit using an intramolecular anomeric protection (iMAP) strategy. The synthesis was completed in 28 steps, including the preparation of building blocks, construction of the tetrasaccharide skeleton, and functional group transformations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Medicinal
Monika Shukla, Komal Rathi, Mohammad Hassam, Dinesh Kumar Yadav, Manvika Karnatak, Varun Rawat, Ved Prakash Verma
Summary: The demand for novel, fast-acting, and effective antimalarial medications is rapidly increasing due to the spread of multidrug resistant forms of malaria parasites. Various strategies have been employed to address drug resistance, including targeted therapies, the hybrid drug idea, and the development of advanced analogues of existing drugs. The 1,2,4-trioxane ring system in artemisinin (ART) has been identified as a key pharmacophoric moiety for the potential of endoperoxide-based antimalarials.
MEDICINAL RESEARCH REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Neelam Sharma, Suman Swami, Sakshi Pathak, Ved Prakash Verma, Rahul Shrivastava
Summary: A simple and efficient method for the synthesis of substituted pyrazole-containing tetrazole derivatives has been developed using sulfonic acid decorated graphene oxide (GO-SO3H) as a catalyst. The GO-SO3H catalyst exhibited high catalytic activity, giving yields of over 95% within 15-20 minutes under mild reaction conditions. The catalyst was also found to be reusable for up to five reaction cycles without significant loss of efficiency. Spectroscopic techniques were used to confirm the structures of the synthesized compounds.
RESEARCH ON CHEMICAL INTERMEDIATES
(2023)
Article
Multidisciplinary Sciences
Mohammad Shahidul Islam, Abdullah Mohammed Al-Majid, Essam Nageh Sholkamy, Assem Barakat, Maurizio Viale, Paola Menichini, Andrea Speciale, Fabrizio Loiacono, Mohammad Azam, Ved Prakash Verma, Sammer Yousuf, Mohamed Teleb
Summary: Recently, clinical-stage spirooxindole-based MDM2 inhibitors have been introduced in cancer research protocols, but tumor resistance to the treatment has been reported. Therefore, researchers have focused on designing various combinatorial libraries of spirooxindoles. In this study, a new series of spirooxindoles were created through the hybridization of a chemically stable core and a pyrazole motif, inspired by lead pyrazole-based p53 activators and promising molecules previously reported. The derivatives were tested for cytotoxic activities on cancer cell lines and some showed potentiation of doxorubicin activity.
SCIENTIFIC REPORTS
(2023)
Review
Chemistry, Multidisciplinary
Garima Sachdeva, Yogita Bamal, Ankit Ladan, Om Shanker Tiwari, Varun Rawat, Priyanka Yadav, Ved Prakash Verma
Summary: The synthesis of polylactide has attracted attention recently due to its biocompatibility and environmental issues associated with fossil-fuel-based polymers. Polylactide can be obtained from natural sources or synthesized in a laboratory using various methods. Lewis acid catalyzed ring-opening polymerization is an effective pathway, and metal-calixarene complexes have been explored as suitable molecular scaffolds for lactide polymerization. This review summarizes the progress in using metal-calixarene complexes for the ring-opening polymerization of lactide.
Article
Chemistry, Organic
Riya Nagar, Dinesh Suwalka, Bhanwar Kumar Malviya, Ved Prakash Verma, Amanpreet Kaur Jassal, Siddharth Sharma
Summary: The combination of the Ugi reaction and electro-organic synthesis has been used to develop a new strategy for the synthesis of novel heterocycles with diverse functional groups. This approach offers high selectivity and is applicable for large-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dinesh Suwalka, Bhanwar Kumar Malviya, Ved Prakash Verma, Amanpreet Kaur Jassal, Siddharth Sharma
Summary: In this study, post-Ugi cyclization reactions were explored using N-centered radical-mediated intramolecular ipso cyclization to synthesize diverse spirocyclic variants of 4-imidazolidinones through the use of electrochemically generated amidyl radicals from the bis-amides of the Ugi adducts. This method features metal- and reagent-free reactions that are scalable and have broad substrate scope.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kuldeep Singh Bhati, Dinesh Suwalka, Ved Prakash Verma, Amanpreet Kaur Jassal, Neetu Kumari, Siddharth Sharma
Summary: This paper presents a simple and efficient electrochemical method to induce structural alterations in 2H-indazole by modulating the cell voltage. The method allows for C-3 acyloxylation of 2H-indazole and facilitates the transfer of the acyl group from C-3 to N-1 for N-acylation of 2H-indazoles. Additionally, the use of the & mu;-electroflow reactor is demonstrated for gram-scale production of 3x in a short residence time.
Article
Chemistry, Multidisciplinary
Chun-Hong Yeh, Ya-Jou Chang, Tsung-Juin Lin, Cheng-Chung Wang
Summary: Infection with Campylobacter jejuni results in severe diarrhea, posing a significant threat to young children in underdeveloped countries. Due to the rise in antibiotic resistance, there is a need to develop a new therapy.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Medicinal
Priyanka Yadav, Niraj Krishna Naikade, Mohammad Hassam, Ajit Shankar Singh, Chandan Singh, Sunil K. Puri, Ved Prakash Verma
Summary: Malaria, categorized as a life-threatening epidemic in underdeveloped countries, has been targeted for eradication by a novel series of synthesized compounds. In mouse models, these compounds demonstrated high protection, with compounds 17a1 and 17a2 proving twice as potent as artemisinin.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
