Review
Chemistry, Multidisciplinary
Sam M. Rowe, David R. Spring
Summary: RiPPs are recognized as a potential source of antimicrobial drugs due to their potent activity and high stability, but issues such as low solubility and poor bioavailability often hinder their clinical development. Chemical synthesis can help overcome some of these challenges, and the structural complexity of RiPPs makes them interesting synthetic targets.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Junyi Wang, Shuai Zhu, Wangyang Ma, Zhenyang Lin, Qing Ye
Summary: BN-butafulvenes, mono-BN isosteres of butafulvene and highly strained isomers of azaborines and B-amino boroles, have been synthesized via hydrolysis of the urana-borabicyclic complexes obtained from the reactions of bis(alkynyl)boranes with an uranacyclopropene complex. Their 4-dimethylaminopyridine (DMAP) adducts can further isomerize to 1,2,4,6-multisubstituted BN-9,1-naphthalenes. Both NMR reaction monitoring and theoretical calculations point to a reaction mechanism involving dearomative insertion of DMAP followed by two consecutive 1,2-hydrogen shifts. The photophysical studies of the highly substituted BN-9,1-naphthalenes reveal a notable redshift in both the UV/Vis absorption and emission spectra. The (TD)-DFT calculations corroborate the experimental data, suggesting that the strong pi-donating amino substitution at the 1- and/or 6-positions destabilizes the HOMO, and thus leading to a notable decrease of the HOMO-LUMO gap.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Mieko Arisawa, Taro Mizuno, Kanako Nozawa-Kumada, Kaori Itto-Nakama, Miyu Furuta, Saori Tanii
Summary: Unsymmetric di(heteroaryl)ureas such as HetAr(1)-NHCONH-HetAr(2) can be efficiently synthesized from two symmetric ureas, HetAr(l)-NHCONH-HetAr(1) and HetAr(2)-NHCONH-HetAr(2), through rhodium-catalyzed exchange reactions. In some reactions, the equilibrium can be shifted to the formation of unsymmetric ureas by the aggregation of dimers formed by inter- and intramolecular hydrogen bonding.
Review
Chemistry, Medicinal
Eslam R. El-Sawy, Gilbert Kirsch
Summary: Marine products, particularly aplysinopsins, are valuable sources of biologically active compounds. Aplysinopsins, derived from various marine organisms such as sponges, corals, sea anemone, and nudibranch, have been isolated from different geographic regions including the Pacific, Indonesia, Caribbean, and Mediterranean. This review provides an up-to-date overview of the sources, synthesis, and biological activities of aplysinopsin derivatives.
Article
Biochemistry & Molecular Biology
David M. Hitt, Jeffery D. Zwicker, Chih-Kai Chao, Sarjubhai A. Patel, John M. Gerdes, Richard J. Bridges, Charles M. Thompson
Summary: The study synthesized a series of Congo Red analogs with one or two glutamate isostere or mimic groups to explore binding interactions within VGLUT; the more potent inhibitors featured two symmetric glutamate isosteres linked to a central aromatic group, showing high activity on VGLUT.
NEUROCHEMICAL RESEARCH
(2021)
Article
Polymer Science
Alexandrina Nan, Teodora Radu, Xenia Filip, Irina Kacso, Niculina Daniela Hadade, Fran Nekvapil, Maria Miclaus
Summary: Recently, there has been great interest in synthesizing polymers with fluorine atoms. This work presents the synthesis, characterization, and properties of a new fluorinated aromatic polyester, Poly(fluoromandelic acid) (PFMA). The polymer chain of PFMA contains multiple fluorine atoms and exhibits high hydrophobicity and good thermal stability.
Article
Chemistry, Organic
Daniel Polyak, Isaac J. Krauss
Summary: An efficient multigram synthesis method for alkynyl amino acid Fmoc-L-homopropargylglycine-OH is described. The optimized Boc protection and Seyferth-Gilbert homologation resulted in high material throughput and avoidance of racemization, respectively. The enantiopure (>98% ee) noncanonical amino acid can be readily generated for solid phase synthesis of functionalized peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhiyun Wu, Weifeng Shi, Ming Jin, Wei Zhou
Summary: Using 1,4-benzodioxane-2-carboxylic acid methyl ester as the substrate, mutants A225F and A225F/T103A were found to catalyze the kinetic resolution of the substrate among 38 CALB covariant residues. The optimal conditions for kinetic resolution were achieved at 30 degrees C with 20% n-butanol as a cosolvent and 50 mM substrate concentration, resulting in an optimal resolution (e.e.(s) 97%, E = 278). Structure analysis revealed that mutation sites 225 and 103 regulate enzyme catalysis remotely, suggesting a new strategy for enzyme evolution.
Article
Biochemistry & Molecular Biology
Sakshi Balasaria, Balaram Mukhopadhyay
Summary: In this study, we chemically synthesized the pentasaccharide repeating unit of E. coli strain SDLZB008's O-antigen using a linear strategy that involved rationally protected monosaccharide derivatives to ensure the desired stereochemistry. We incorporated a 2-aminoethyl glycoside at the reducing end of the pentasaccharide, allowing the terminal free amine to be used for further conjugation without affecting the stereochemistry at the reducing end. Additionally, we successfully incorporated the rare D-Fucp3NAc moiety using a 3-azido derivative derived from a known 3-azido quinovose derivative.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Boris Smolkin, Noam Levi, Ravit Chen
Summary: This study developed an active solid composite matrix for HD decontamination via oxidation, converting it into a non-toxic sulfoxide within minutes, which could be easily removed from the site with water, resulting in less environmental damage.
Article
Chemistry, Multidisciplinary
Huiting Li, Hongzhao Mao, Chao Chen, Ying Xu, Shuai Meng, Tiantian Sun, Chengli Zong
Summary: This study demonstrates the successful alpha-selective glycosylation using a bulky DTBS galactosyl donor, overcoming the challenge of the difficult alpha-1,2-cis-glycosidic bond. The use of azide for the C-6 modification also provides potential for further functionalization through click chemistry or easy transformation to other functional groups.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Boris Smolkin, Noam Levi, Ravit Chen
Summary: In this study, a new active solid composite matrix was designed and developed for the efficient sorption and detoxification of chemical warfare agents. The composite material showed high efficiency in sorbing and oxidizing HD, resulting in less environmental damage and quick remediation.
Article
Biochemistry & Molecular Biology
Naoko Abe, Akihiro Imaeda, Masahito Inagaki, Zhenmin Li, Daisuke Kawaguchi, Kaoru Onda, Yuko Nakashima, Satoshi Uchida, Fumitaka Hashiya, Yasuaki Kimura, Hiroshi Abe
Summary: A fast and quantitative chemical capping reaction method was developed to prepare capped RNA. It was found that mRNAs with non-nucleotide linkers showed sufficient tolerance to translation and mRNAs with the Cap_2 structure had higher translational activity than those with the Cap_0 structure.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Organic
Tingting Cui, Wen-Jie Li, Junyou Chen, Rui Zhao, Yi-Ming Li
Summary: The hydrazide-based native chemical ligation-assisted diaminodiacid (DADA) strategy is an efficient method for synthesizing large-span disulfide bridge surrogates. However, it is difficult to synthesize disulfide bond surrogates at Gln-Cys or Asn-Cys ligation sites using this strategy. In this study, a peptide o-aminoanilide-mediated NCL-assisted DADA strategy is reported, enabling the synthesis of large-span peptide disulfide bridge surrogates containing only Gln-Cys or Asn-Cys ligation sites.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lingbowei Hu, Viresh H. Rawal
Summary: Reported is the total synthesis of (+)-ambiguine G, the first member of the chlorinated pentacyclic ambiguines to be obtained through chemical synthesis. The synthesis involves a convergent strategy starting from (S)-carvone oxide and proceeding in 10 steps, with a key [4+3] cycloaddition and efficient, diastereoselective construction of a key vinylated chloro ketone. An unprecedented one-pot reduction-elimination-oxidation sequence is also featured, transforming an enone to an advanced hydroxylated-diene intermediate.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Zebediah C. Girvin, Laura F. Cotter, Hyung Yoon, Steven J. Chapman, James M. Mayer, Tehshik P. Yoon, Scott J. Miller
Summary: High selectivity in photochemical reactions can be achieved by controlling the transition state.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Sooyun Choi, Melody C. Guo, Gavin M. Coombs, Scott J. Miller
Summary: An atroposelective synthesis method for N-aryl 1,2,4-triazoles was developed. By utilizing a chiral phosphoric acid catalyst, a cyclodehydration reaction achieved asymmetric induction, resulting in atropisomeric N-aryl 1,2,4-triazoles with up to 91:9 enantiomeric ratio. Further crystallization of the isolated heterocycle enhanced the atropisomeric ratio of several analogs to 99:1 or higher. Additionally, a divergent and substrate-dependent reaction pathway leading to a different heterocyclic product was revealed.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Multidisciplinary
Marisa C. Kozlowski, Scott J. Miller, Stephane Perreault
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Editorial Material
Chemistry, Inorganic & Nuclear
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, PrashantV. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
INORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Organic
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zoe L. Watson, Isaac J. Knudson, Fred R. Ward, Scott J. Miller, Jamie H. D. Cate, Alanna Schepartz, Ara M. Abramyan
Summary: As genetic code expansion progresses, it is still a challenge to determine the substrates the ribosome can accommodate. This study provides insights into how the E. coli ribosome incorporates non-?-a-amino acids, using high-resolution cryogenic electron microscopy and metadynamics simulations. The findings suggest that reactive monomers prefer a specific conformational space for efficient bonding, which could facilitate the synthesis of non-peptide heterooligomers.
Editorial Material
Chemistry, Organic
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
Article
Multidisciplinary Sciences
Jonas Rein, Soren D. Rozema, Olivia C. Langner, Samson B. Zacate, Melissa A. Hardy, Juno C. Siu, Brandon Q. Mercado, Matthew S. Sigman, Scott J. Miller, Song Lin
Summary: We have developed a catalytic enantioselective method for the oxidative desymmetrization of meso-diols. This method is generally applicable to a broad range of substrates and involves the optimization of a nontraditional catalyst through screening a panel of substrates. By rational modulation of a peptide sequence in the catalyst, a general catalyst with high selectivity and turnover was obtained.
Editorial Material
Chemistry, Physical
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
Editorial Material
Chemistry, Physical
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson
ACS ENERGY LETTERS
(2023)
Editorial Material
Chemistry, Analytical
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
ACS MEASUREMENT SCIENCE AU
(2023)
Editorial Material
Chemistry, Multidisciplinary
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
ACS ORGANIC & INORGANIC AU
(2023)
Article
Chemistry, Organic
Susannah E. Huth, Elizabeth A. Stone, Simone Crotti, Scott J. Miller
Summary: During the study of peptide-catalyzed N-oxidations of pyridines, we observed unexpectedly low barriers to atropisomerization under the reaction conditions. Mechanistic studies revealed a hydrogen bond-assisted racemization mechanism inherent to both the starting materials and products. Additionally, a protonation-dependent barrier to rotation was identified for the starting materials alone. Despite this, several substrates could undergo atroposelective N-oxidations via kinetic resolution, with some achieving high enantiomeric ratios (>99:1) after recrystallization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Benjamin G. Hejna, Jacob M. Ganley, Huiling Shao, Haowen Tian, Jonathan D. Ellefsen, Nicholas J. Fastuca, Kendall N. Houk, Scott J. Miller, Robert R. Knowles
Summary: We present a highly enantioselective radical-based hydroamination of enol esters with sulfonamides using an Ir photocatalyst, Bronsted base, and tetrapeptide thiol. The reaction produces 23 protected β-amino-alcohol products with selectivities up to 97:3 er. Experimental and computational studies reveal that hydrogen bonding, π-π stacking, and London dispersion interactions play important roles in substrate recognition and enantioinduction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jongdoo Lim, Melody Guo, Sooyun Choi, Scott J. Miller, Eric V. Anslyn
Summary: Atropisomeric scaffolds are commonly found in pharmaceuticals and their handedness is crucial for their efficacy and safety. To keep up with the fast workflow of high-throughput screening for drug discovery, a rapid enantiomeric excess (ee) analysis method based on circular dichroism (CD) was developed for N-C axially chiral triazole derivatives. The CD assay showed accurate and efficient ee determination with minimal errors.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
