Article
Chemistry, Multidisciplinary
Yuqin Wang, Pingping Fan, Shanyu Zhang, Liying Wang, Xinyue Li, Wendong Jia, Yao Liu, Kefan Wang, Xiaoyu Du, Panke Zhang, Shuo Huang
Summary: In this study, a specially engineered nanopore sensor was used to successfully discriminate all canonical ribonucleoside mono-, di-, and triphosphates, and a machine-learning algorithm was developed with a general accuracy of 99.9% for ribonucleotide sensing. This sensing strategy was also applied to identify ribonucleotide components in different phosphorylated forms.
Article
Biochemistry & Molecular Biology
Katja F. Hellendahl, Felix Kaspar, Xinrui Zhou, Zhaoyi Yang, Zhen Huang, Peter Neubauer, Anke Kurreck
Summary: By optimizing the synthesis of selenium-modified nucleosides using thermostable nucleoside phosphorylases in transglycosylation reactions with natural nucleosides as sugar donors, the study achieved isolated yields of Se-containing nucleosides in 6-40%. However, the unfavorable thermodynamic properties of the nucleosides required a tenfold excess of sugar donor for conversion, complicating the synthesis process.
Article
Chemistry, Multidisciplinary
Qingfeng Li, Victoria A. Maola, Nicholas Chim, Javeena Hussain, Adriana Lozoya-Colinas, John C. Chaput
Summary: This study expands the chemical space of evolvable nucleic acid systems by introducing diverse functional groups at the C-5 position of alpha-L-threofuranosyl uridine nucleoside triphosphate (tUTP), providing a synthetic route to therapeutic aptamers with high biological stability. Structural insights into TNA synthesis were obtained from a high-resolution X-ray crystal structure analysis, revealing a large cavity in the enzyme active site that accommodates the modification of tUTP substrates. The findings offer a promising route to artificially modified genetic polymers uniformly enhanced with diversity-enhancing functional groups.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Jianxi Ying, Ruiwen Ding, Yumeng Zhang, Bowen Han, Yeting Guo, Ning Wang, Dandan Guo, Yile Wu, Junwei Huang, Yan Liu, Feng Ni, Shaohua Huang, Yufen Zhao
Summary: This study reveals the mechanism of chiral selection in Earth's life and suggests the existence of a chiral system opposite to that on Earth, implying a world of life that is a complete mirror image of Earth.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Medicinal
Yuqing Xu, Elisabetta Groaz, Jerome Rihon, Piet Herdewijn, Eveline Lescrinier
Summary: Molecular dynamics simulations revealed the favorable interactions between xylose nucleosides with a phosphonate moiety and specific residues at the active site of the RNA-dependent RNA-polymerase of Enterovirus 71. Xylosyl nucleoside phosphonates containing different nucleobases were synthesized and tested for antiviral activity, with the adenine-containing analogue showing good activity against measles virus and enterovirus-68 without cytotoxicity.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Jie-Hui Zhang, Cheng-Lin Pan, Huan-Huan Zhang, Peng-Fei Xu, Yong-Chun Luo
Summary: A Sc(OTf)3 catalyzed [3 + 2]-annulation reaction has been developed for the conversion of donor-acceptor aziridines and exo-glycals into carbohydrate-spiro-heterocycles, yielding proline analogues and polycyclic compounds. This reaction also revealed the stereochemistry characteristic of the reaction between racemic D-A aziridines and chiral enolethers.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Mikhail S. Drenichev, Vladimir E. Oslovsky, Anastasia A. Zenchenko, Claudia V. Danilova, Mikhail A. Varga, Roman S. Esipov, Dmitry D. Lykoshin, Cyril S. Alexeev
Summary: A comparative analysis was conducted on the transglycosylation conditions catalyzed by E. coli nucleoside phosphorylases, leading to the formation of 2'-deoxynucleosides. The study demonstrated that maximal yields of modified 2'-deoxynucleosides can be achieved with a slight excess of carbohydrate residue donor nucleoside and a four-fold lack of phosphate.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Blazej A. Wojtczak, Marcelina Bednarczyk, Pawel J. Sikorski, Anna Wojtczak, Piotr Surynt, Joanna Kowalska, Jacek Jemielity
Summary: Chemical modifications of the mRNA cap structure can improve the therapeutic properties of synthetic mRNA by enhancing stability, translational properties, and half-life. The Suzuki-Miyaura cross-coupling reaction is a useful approach for modifying cap structures, and two methods for synthesizing C8-modified cap structures using this reaction were described. The modified cap structures were successfully used to study the interaction with cap-binding proteins.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sandeep Kumar, Sumit Kumar, Jyotirmoy Maity, Banty Kumar, Shilpika Bali Mehta, Ashok K. Prasad
Summary: The Groebke-Blackburn-Bienayame (GBB) reaction is efficiently used for synthesizing novel fluorescent 5-azaindolizino-2'-deoxyuridines from commercially available thymidine. These synthesized compounds show strong fluorescence properties and have potential applications in studying the local structure and dynamics of nucleic acids.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Chiara Figazzolo, Frederic Bonhomme, Saidbakhrom Saidjalolov, Melanie Etheve-Quelquejeu, Marcel Hollenstein
Summary: The emergence of drug-resistant strains has led to the failure of many potent antibiotics in treating bacterial infections. This article presents a novel approach of using nucleotides connected to antibiotics to identify aptamers that can restore the bactericidal activities of drugs. The authors report the synthesis of a modified nucleoside triphosphate and demonstrate its compatibility with SELEX methodology, opening up possibilities for identifying vancomycin-modified aptamers.
Article
Chemistry, Organic
Ying-Ying Dong, Hua-Shan Huang, Ren-Yuan Zhong, Shan-Shan Gong, Qi Sun
Summary: α-P-modified nucleoside triphosphates (NTP alpha Xs), an important class of nucleoside triphosphate analogues, have been recognized as versatile tools in molecular biology and medicinal chemistry. However, the available synthetic methods for NTP alpha Xs are only low to moderate-yielding. In this study, we developed a new method based on linear (PPPIII)-P-V-P-V-nucleoside intermediates to access NTP alpha Xs.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Aleksandra Trocha, Dorota G. G. Piotrowska, Iwona E. E. Glowacka
Summary: This study developed simple and efficient strategies for synthesizing enantiomerically enriched functionalized diethyl 2-amino-, 2,3-diamino- and 2-amino-3-hydroxypropylphosphonates. Starting from N-protected (aziridin-2-yl)methylphosphonates, a regioselective aziridine ring-opening reaction with corresponding nucleophiles was employed. The reactions resulted in the formation of various phosphonate derivatives with high enantiomeric purity.
Article
Biochemistry & Molecular Biology
Alexey L. Kayushin, Julia A. Tokunova, Ilja V. Fateev, Alexandra O. Arnautova, Maria Ya. Berzina, Alexander S. Paramonov, Olga I. Lutonina, Elena V. Dorofeeva, Konstantin V. Antonov, Roman S. Esipov, Igor A. Mikhailopulo, Anatoly I. Miroshnikov, Irina D. Konstantinova
Summary: This study investigates the issues encountered during the preparative synthesis of 2-fluorocordycepin, as well as the impact of unknown nucleoside formation on the reaction. The hydrolysis mechanism of 2',3'-anhydroinosine in D2O is fully determined for the first time in this research, shedding light on its inhibitory effects on the synthesis of 2-fluorocordycepin.
Article
Chemistry, Organic
Yong Gong, Wei Zhang, Lu Chen, Ronghui Lin, Ronghui Zhou, Rhys Salter
Summary: This study demonstrates the preparation of functionalized nucleosides bearing pyrimidine or purine bases through nitration reactions, expanding the synthetic methods for related compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Maria De Fenza, Anna Esposito, Daniele D'Alonzo, Annalisa Guaragna
Summary: The de novo synthesis of piperidine nucleosides from 5,6-dihydro-1,4-dithiin was reported, with the NMR analysis confirming the iminosugar conformation of the synthesized compounds.