Article
Biochemistry & Molecular Biology
Kavita Singh, Sourav Sagar Behera, Rajdeep Tyagi, Ghanshyam Tiwari, Ram Sagar
Summary: A metal free synthesis of enantiopure 2,3-dideoxy-α, β-unsaturated carbohydrate enals (Perlin aldehydes) in CH3CN-0.02 N H2SO4 in water (1:1, v/v) with additives has been reported. The protocol works well for acetylated glycals, providing Perlin aldehydes and hemiacetals in good yields. The use of 0.02 N H2SO4 in water: acetonitrile (1:1, v/v) solvent system is essential for Perlin aldehyde formation.
CARBOHYDRATE RESEARCH
(2023)
Article
Biochemistry & Molecular Biology
Xueying You, Yifei Cai, Chenyu Xiao, Lijuan Ma, Yong Wei, Tianpeng Xie, Lei Chen, Hui Yao
Summary: An effective and direct methodology using AgOTf as a catalyst has been developed for the stereoselective synthesis of alpha-2-deoxythioglycosides. This method not only allows the synthesis of disaccharides, but also enables successful late-stage glycosylation of estrogen, L-menthol, and zingerone with thiol compounds.
Article
Chemistry, Organic
Irshad Ahmad Zargar, Norein Sakander, Debaraj Mukherjee
Summary: A strategy was designed for the synthesis of regioselective and stereoselective displacement of C-3 acetate group in the presence of other C-4 and C-6 acetate of 2-ketophenyl-glycal by different aromatic and cyclic aliphatic thiol nucleophiles, inspired by cytosolic esterase mediated thiolation of glucosamine sugars. The protocol achieved the removal of C-3 acetate group and maintained high axial selectivity, resulting in a library of 3-arylthiosugars with excellent yields. This stereoselective approach showed tolerance to different ester-protected glycals and thiophenols, aliphatic cyclic thiols, and mercaptans. Control experiments were conducted to establish the mechanism and reason behind the stereoselectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Matthew G. Dowgiallo, Brandon C. Miller, Mintesinot Kassu, Kenneth P. Smith, Andrew D. Fetigan, Jason J. Guo, James E. Kirby, Roman Manetsch
Summary: This article describes a convergent and diversity-enabling total synthesis of streptothricin F, a natural product. The synthesis allows for the installation of practical divergent steps for medicinal chemistry applications and enables the evaluation of the potent antimicrobial activity of streptothricin F.
Article
Chemistry, Organic
Wei-Yi Ding, Hao-Wen Zhao, Jun Kee Cheng, Zhiqiang Lu, Shao-Hua Xiang, Bin Tan
Summary: This report describes a highly efficient beta-selective C-glycosylation reaction using bicyclic galactals and 2-oxindoles as substrates. The reaction proceeds through a palladium-catalyzed decarboxylative pathway under mild reaction conditions, resulting in high yields. The decarboxylation intermediate of galactal acts as an efficient base to deprotonate the enol tautomer of 2-oxindole, enhancing its nucleophilicity. The beta-selective nucleophilic addition at the anomeric center is due to steric hindrance imposed by the palladium and bulky ligand.
Article
Chemistry, Organic
Kim Greis, Caleb E. Griesbach, Carla Kirschbaum, Gerard Meijer, Gert von Helden, Kevin Pagel, Mark W. Peczuh
Summary: Ferrier reactions involve Lewis acid activation of a cyclic enol ether to generate a glycosyl Ferrier cation through the departure of an allylic leaving group. The resulting cation undergoes attack and transposition, forming a new acetal linkage. This study focuses on the septanosyl Ferrier cation derived from a seven-membered ring carbohydrate-based oxepine. Experimental characterization of the ion, including gas-phase cryogenic IR spectroscopy and solution-phase Ferrier reactions, reveals a preference for contraction to five-membered ring structures in the cation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lisi Yuan, Ya Fang, Zhaobo Zhou, Tinghong Lv, Yingpeng Su, Jian Liu, Xiaolei Wang
Summary: This Letter describes a highly diastereoselective synthesis method for C-hydroxymethine glycosides from glycal anomers using an achiral N-heterocyclic carbene-copper catalyst. The diastereoselectivity is controlled by both the stereocenter of the substrate and the chirality of the N-heterocyclic carbene-copper complex, independent of the stereochemistry of C5 and the anomeric position. This approach allows for the production of a diverse range of C-hydroxymethine glycosides using versatile glycals and various functionalized aldehydes.
Article
Biochemistry & Molecular Biology
Lisa Ngu, Debarpita Ray, Samantha S. Watson, Penny J. Beuning, Mary Jo Ondrechen, George A. O'Doherty
Summary: A diastereoselective synthesis of the beta-anomer of glycinamide ribonucleotide (beta-GAR) has been developed with a high overall yield. The synthetic beta-GAR demonstrated remarkable resistance to anomerization in both solution and solid state.
Article
Chemistry, Multidisciplinary
Fen Liu, Haiyang Huang, Longgen Sun, Zeen Yan, Xiao Tan, Jing Li, Xinyue Luo, Haixin Ding, Qiang Xiao
Summary: Glycals are versatile building blocks in carbohydrate and natural product chemistry. A new method for the synthesis of glycals using phosphonium hydrolysis-induced intermediate-mediated reactions is presented. The method is highly efficient and applicable to late-stage modification of complex drug-like molecules.
Article
Chemistry, Organic
Wang Jingrui, Feng Yongkui, Wang Nengzhong, Huang Nianyu, Yao Hui
Summary: C-Glycosides have attracted attention in the fields of medicine and biology due to their physiological activities and stability. This paper reports a method for preparing high stereoselectivity beta-C-glycosides through a specific reaction at room temperature, providing a reliable method for the rapid construction of C-glycoside libraries.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pradip Das, Mosidur Rahaman Molla, Amit Kumar, Rima Thakur
Summary: The study reports an efficient and stereoselective synthesis of 2,3-dideoxy-beta-O-glycosides from C3-(o-cyanobenzoate) ester protected glycal donors via Ferrier rearrangement under Pd(0)-catalyzed Tsuji-Trost conditions. The stereo-chemical outcome of the reactions was independent of the nature of protecting groups or conformational flexibility of the glycal donors. Incorporation of the directing group on the benzoate ester altered the reactivity for Tsuji-Trost as well as Ferrier Rearrangement pathway.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Maria Laura Uhrig, Erwin W. Mora Flores, Al Postigo
Summary: Fluoroalkyl-substituted carbohydrates play important roles in wetting, antifreeze, and coating agents, and are significant to the synthetic carbohydrate community. This study summarizes the methods for installing R-F groups onto carbohydrates and derivatives, as well as presents new advances in the synthesis of fluoroalkyl-substituted iminosugars.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Bryant Pero, Mark W. Peczuh
Summary: A new synthesis of carbohydrate-based oxepines using 2,3;4,6-di-O-acetonide mannose as a key starting material is reported. The oxepine is an important precursor used in the synthesis of septanose glycomimetics of mannopyranosides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yong-Wang Huo, Xinxin Qi, Xiao-Feng Wu
Summary: This study developed a new method for synthesizing alpha,beta-unsaturated thioesters via nickel-catalyzed thiocarbonylation reaction of vinyl triflates with arylsulfonyl chlorides. By using Mo(CO)(6) as both CO source and reductant, alpha,beta-unsaturated thioesters were obtained in moderate to good yields with excellent functional group compatibility. It is notable that this is the first example of nickel-catalyzed carbonylative synthesis of alpha,beta-unsaturated thioesters using arylsulfonyl chlorides as the coupling partner.
Article
Chemistry, Organic
Shashank Tripathi, Monty Kumar, Mayur D. Ambule, Ankit Saxena, Ruchir Kant, Sanjeev K. Shukla, Ajay Kumar Srivastava
Summary: Stereoselective difunctionalizations of alkynes were achieved to prepare (Z)-/(E)-fi-sulfonylacrylamides. The (Z)-fi-sulfonylacrylamides were generated via a one-pot process, while the (E)-fi-sulfonylacrylamides were prepared in a two-step synthesis.
Article
Chemistry, Organic
Lucilla Favero, Paolo Crotti, Valeria Di Bussolo, Elio Napolitano
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Gloria Uccello Barretta, Federica Balzano, Federica Aiello, Francesca Nardelli, Alessia Ciogli, Andrea Calcaterra, Bruno Botta
SUPRAMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Valeria Di Bussolo, Salvatore Princiotto, Elisa Martinelli, Vittorio Bordoni, Paolo Crotti
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Organic
Federica Aiello, Federica Balzano, Francesca Ghirga, Ilaria D'Acquarica, Bruno Botta, Gloria Uccello-Barretta, Deborah Quaglio
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Cinzia Chiappe, Gian Carlo Demontis, Valeria Di Bussolo, Maria Jesus Rodriguez Douton, Francesco Rossella, Christian Silvio Pomelli, Stefania Sartini, Stefano Caporali
Article
Chemistry, Organic
Valeria Di Bussolo, Ileana Frau, Lucilla Favero, Vittorio Bordoni, Stefano Crotti, Gloria Uccello Barretta, Federica Balzano, Paolo Crotti
Article
Chemistry, Organic
Salvatore Princiotto, Valeria Di Bussolo, Vittorio Bordoni, Lucilla Favero, Stefano Crotti, Gloria Uccello Barretta, Federica Balzano, Paolo Crotti
Article
Chemistry, Organic
Francesco Berti, Andrea Menichetti, Valeria Di Bussolo, Lucilla Favero, Mauro Pineschi
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2018)
Article
Pharmacology & Pharmacy
Angela Fabiano, Anna Maria Piras, Gloria Uccello-Barretta, Federica Balzano, Andrea Cesari, Lara Testai, Valentina Citi, Ylenia Zambito
EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS
(2018)
Article
Chemistry, Multidisciplinary
Sofia Masi, Federica Aiello, Andrea Listorti, Federica Balzano, Davide Altamura, Cinzia Giannini, Rocco Caliandro, Gloria Uccello-Barretta, Aurora Rizzo, Silvia Colella
Article
Chemistry, Medicinal
Michela Vargiu, Lucilla Favero, Andrea Menichetti, Valeria Di Bussolo, Fabio Marchetti, Gennaro Pescitelli, Sebastiano Di Pietro, Mauro Pineschi
Article
Biochemistry & Molecular Biology
Felicia D'Andrea, Giulia Vagelli, Carlotta Granchi, Lorenzo Guazzelli, Tiziano Tuccinardi, Giulio Poli, Dalila Iacopini, Filippo Minutolo, Valeria Di Bussolo
Article
Chemistry, Organic
Valeria Di Bussolo, Salvatore Princiotto, Vittorio Bordoni, Elisa Martinelli, Lucilla Favero, Stefano Crotti, Gloria Uccello-Barretta, Federica Balzano, Mauro Pineschi, Paolo Crotti
Article
Biochemistry & Molecular Biology
Sebastiano Di Pietro, Dalila Iacopini, Aldo Moscardini, Ranieri Bizzarri, Mauro Pineschi, Valeria Di Bussolo, Giovanni Signore
Summary: This study introduces two new tris coumarin-dipicolinate europium (III) complexes, which can be tailored to be either mono or dual emitters and their properties tuned with simple chemical modifications. The research also reveals a rich chemical speciation in solution, which is studied in detail by paramagnetic NMR and emission spectroscopy.
Article
Chemistry, Multidisciplinary
Manuela Curcio, Alessandro Paoli, Giuseppe Cirillo, Sebastiano Di Pietro, Martina Forestiero, Francesca Giordano, Loredana Mauro, Diana Amantea, Valeria Di Bussolo, Fiore Pasquale Nicoletta, Francesca Iemma
Summary: This study successfully prepared new dual pH/redox-responsive nanoparticles with affinity for folate receptors, demonstrating potential applicability as a new drug vector in cancer therapy.
