Article
Chemistry, Organic
Clara Sgorbati, Eliana Lo Presti, Greta Bergamaschi, Monica Sani, Alessandro Volonterio
Summary: The solid-phase synthesis of Gly-Psi[CH(CF3)NH]-peptides has been developed, resulting in a small library of six peptidomimetics with high purity, analogues of biologically relevant peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Satish Kumar, Kshetrimayum Borish, Sanjit Dey, Jayashree Nagesh, Aloke Das
Summary: The folding motifs of Gly-Pro and Pro-Gly dipeptides were investigated and their structures were found to be dependent on the hydrogen bonding interactions. The structure of Gly-Pro peptide was consistent between gas phase and solution phase, while the Pro-Gly peptide had different structures in gas phase and solution phase. Solvent might play a crucial role in dictating the preferential stabilization of the C10 structure in the solution phase.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Biochemistry & Molecular Biology
Meng-Che Li, Ying-Jie Liu, Kuang-Cheng Hsu, Tse-Hsueh Lin, Chih-Wei Lin, Jia-Cherng Horng, Sheng-Kai Wang
Summary: This article investigates how the interaction between fluorine atoms alters protein structures and develops approaches to synthesize fluorinated peptides. The study systematically explores the effects of the number, location, and types of fluorine groups on the conformation of polyproline peptides.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Leiyang Lv, Ge Gao, Yani Luo, Kuantao Mao, Zhiping Li
Summary: The study developed a three-component assembly method under transition-metal-free and open-air conditions for the construction of various 5-amino NH-1,2,3-triazoles, offering a simple and widely applicable approach. It was also demonstrated that NH-1,2,3-triazoles can be smoothly converted to regiospecific N-2 alkylated 1,2,3-triazole products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Clement A. Sanchez, Charlene Gadais, Gregory Chaume, Sylvaine Girard, Evelyne Chelain, Thierry Brigaud
Summary: The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline involves key steps such as Ruppert-Prakash reagent addition on L-pyroglutamic esters, followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.
Article
Chemistry, Inorganic & Nuclear
Julia Mahrholdt, Eduard Kovalski, Tobias Rueffer, Valerije Vrcek, Heinrich Lang
Summary: The reaction between FcC(O)CH=C(OH)R and 1-H2N-4-R'-C6H4 produces β-ketoamines, and their reversible redox processes are determined through electrochemical studies. Electrostatic interactions between Fc/[Fc](+) during oxidation are confirmed by UV/vis-NIR spectroscopy. A linear relationship between s Hammett constants and reversible redox processes is observed.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hajer Ayachi, Houda Gazzeh, Taoufik Boubaker, Jean-Claude Guillemin
Summary: The key compounds (Z)- and (E)-iminoacetonitriles (NCCH=NH), which are hydrogen cyanide dimers, play important roles in prebiotic chemistry. Methylenecyanamide (CH2=NCN), the second most thermodynamically stable dimer of HCN with covalent bonds, has been poorly studied. We demonstrate that this compound can be isolated, forms stable adducts with nucleophiles or dienes, and can be easily generated under prebiotic conditions, suggesting a potential role in this environment. Comparison between isomers reveals significant differences in formation and chemical reactivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Shazia Asghar, Shahid Hameed, Muhammad Nawaz Tahir, Muhammad Moazzam Naseer
Summary: Synthetic s-triazine derivatives have been synthesized through nucleophilic substitution reactions and characterized for their solid-state structures. The compounds exhibit intriguing molecular duplexes driven by hydrogen bonds, which could have potential applications in supramolecular chemistry and crystal engineering.
ROYAL SOCIETY OPEN SCIENCE
(2022)
Review
Chemistry, Multidisciplinary
Michael Andresini, Arianna Tota, Leonardo Degennaro, James A. Bull, Renzo Luisi
Summary: In recent years, there has been a significant increase in the use of sulfoximines in the field of chemistry, as they are considered valuable motifs in medicinal chemistry, due to pioneering works in clinical trials and the development of synthetic methods. Recent developments in sulfoximine synthesis, focusing on S-N and S-C bond formations since 2015, as well as the use of flow chemistry processes and subsequent transformations, particularly in N-functionalization, have been covered in this review.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Christian D. -T. Nielsen, Filip G. Zivkovic, Franziska Schoenebeck
Summary: The study reported a synthetic method for N-trifluoromethyl alkynamides and found that this synthetic compound can serve as a platform to unlock access to other valuable derivatives.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yi Yang, Nathalie Saffon-Merceron, Julien C. Vantourout, Anis Tlili
Summary: We present a straightforward strategy for synthesizing unprecedented N-((trifluoromethyl)thio), N-(trifluoromethyl) amines using isothiocyanates, a fluoride source, and an electrophilic trifluoromethylthiolation reagent. The scalability of the methodology has been demonstrated, and the stability of the synthesized motif has been investigated.
Article
Chemistry, Multidisciplinary
In Gyu Bak, Chang-Guen Chae, Jieun Choi, Woo-Young Song, Jiwon Seo, Eunji Lee, Jae-Suk Lee
Summary: The amphiphilic conformation of alpha-helical peptides, with important biological functions, can be mimicked by alternating polyisocyanate copolymers. The benzyl group of SMBIC and the alkene group of AIC play crucial roles in the alternating copolymerization process, resulting in copolymers with controlled molecular weight and narrow dispersity. N-P(AIC-alt-SMBIC)s were synthesized from thiol-ene radical addition with P(AIC-alt-SMBIC).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Luhan Zhai, Masayuki Nara, Yuko Otani, Tomohiko Ohwada
Summary: NH-pi and CH-pi interactions, which are weak in nature, are not easily detected in solution. However, a group of isolable short peptides with stable folds have been reported, in which these interactions can be identified using NMR and ATR-IR spectroscopy.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Ae Ran Lim, A. Young Kim
Summary: Organic-inorganic hybrid perovskites show great potential for use in various electrochemical devices. In this study, [NH3(CH2)6NH3]CdCl4 crystals were grown and their phase transition temperatures were determined. The crystallographic structure of the cation near TC1 remained unchanged, while that of the anion showed significant changes around 113Cd.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biochemistry & Molecular Biology
Haiyue Long, Ji Xiao, Xiaohui Wang, Minting Liang, Yapei Fan, Yuying Xu, Mengting Lin, Zhe Ren, Chaoxi Wu, Yifei Wang
Summary: Chemical modification of polysaccharides can alter their conformation and properties, with different derivatives exhibiting varying antiviral activities.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Biochemical Research Methods
Zoia Shedania, Rusudan Kakava, Alessandro Volonterio, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2018)
Article
Pharmacology & Pharmacy
Nina Bono, Chiara Pennetta, Aurora Sganappa, Elisa Giupponi, Francesco Sansone, Alessandro Volonterio, Gabriele Candiani
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2018)
Article
Biochemical Research Methods
Lia Bezhitashvili, Anna Bardavelidze, Antonina Mskhiladze, Mehmet Gumustas, Sibel A. Ozkan, Alessandro Volonterio, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2018)
Article
Chemistry, Multidisciplinary
Nina Bono, Chiara Pennetta, Maria Cristina Belluci, Aurora Sganappa, Chiara Malloggi, Gabriella Tedeschi, Gabriele Candiani, Alessandro Volonterio
Article
Biochemical Research Methods
Zoia Shedania, Rusudan Kakava, Alessandro Volonterio, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2020)
Article
Chemistry, Applied
Maria Cristina Bellucci, Alessandro Sacchetti, Alessandro Volonterio
ACS COMBINATORIAL SCIENCE
(2019)
Article
Biochemical Research Methods
Salome Pantsulaia, Khatia Targamadze, Nana Khundadze, Qetevan Kharaishvili, Alessandro Volonterio, Michael Chitty, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2020)
Review
Infectious Diseases
Maria Cristina Bellucci, Alessandro Volonterio
Article
Biochemical Research Methods
Chiara Pennetta, Nina Bono, Federica Ponti, Maria Cristina Bellucci, Fiorenza Viani, Gabriele Candiani, Alessandro Volonterio
Summary: This study describes the design and synthesis of a novel class of aminoglycoside (AG)-based multifunctional vectors with high transfection efficiency and noticeable antibacterial properties. The results demonstrate excellent DNA condensation ability, good transfection performance with negligible cytotoxicity, as well as strong potential as antimicrobial agents.
BIOCONJUGATE CHEMISTRY
(2021)
Article
Chemistry, Organic
Eliana Lo Presti, Alessandro Volonterio, Monica Sani
Summary: This work reports the first synthesis of the complex amino acid labionin in a fully orthogonally protected and stereopure form. The structure incorporates five orthogonal protecting groups and three stereogenic centers, assembled using thia-Michael addition and electrophilic azidation. The successful synthesis is expected to enable the solid phase synthesis of both natural and synthetic analogues of labyrinthopeptins.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Alessio M. Caramiello, Maria Cristina Bellucci, Gaetano Cristina, Carlo Castellano, Fiorella Meneghetti, Matteo Mori, Francesco Secundo, Fiorenza Viani, Alessandro Sacchetti, Alessandro Volonterio
Summary: This study presents the synthesis of a collection of enantiomerically pure, systematically substituted hydantoins as structural privileged universal mimetic scaffolds. The synthesis relies on a selective condensation/cyclization process between isocyanates and aspartic acid diesters, followed by hydrolysis/coupling reactions with amines. Conformational studies showed that the hydantoin-based peptidomimetics are capable of projecting their substituents in positions superimposable to common protein secondary structures.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemical Research Methods
Carola Romani, Paola Gagni, Mattia Sponchioni, Alessandro Volonterio
Summary: In this study, we successfully functionalized PAMAM G2 and PAMAM G4 with fluorinated arginine-based building blocks, resulting in a novel PAMAM-based gene delivery vector. The conjugates showed improved binding capacity to plasmid DNA, reduced cytotoxicity, and enhanced gene transfection efficiency compared to undecorated PAMAM dendrimers. These findings are of great importance for gene delivery research and also have the potential for future application in F-19 magnetic resonance imaging.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Organic
Alessio M. Caramiello, Maria Cristina Bellucci, Emerenziana Ottaviano, Silvia Ancona, Elisa Borghi, Alessandro Volonterio
Summary: Three model hydantoin-based universal peptidomimetics were designed, synthesized, and investigated for their conformation and antibacterial activity. The results demonstrated that these compounds could be promising antibiotics to combat drug resistance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Alessio M. Caramiello, Maria Cristina Bellucci, Emerenziana Ottaviano, Silvia Ancona, Elisa Borghi, Alessandro Volonterio
Summary: In this study, three model hydantoin-based universal peptidomimetics were designed, synthesized, and investigated for their antibacterial activities against Gram-positive and Gram-negative bacteria strains. The results demonstrated that these compounds could potentially serve as promising antibiotics to combat emerging drug resistance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kaivin Hadidi, Maria Cristina Bellucci, Sergio Dall'Angelo, Alasdair Leeson-Payne, Justin J. Rochford, Jeffery D. Esko, Yitzhak Tor, Alessandro Volonterio
Summary: Guanidinoglycosides are non-cytotoxic molecular transporters capable of delivering high molecular weight bioactive cargos into cells at low nanomolar concentrations. The use of a stable guanidinoneomycin derivative armed with a highly specific maleimide moiety allows for efficient bioconjugation through thiol-maleimide click chemistry, expanding the field of application for these delivery vehicles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
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)