Article
Biochemistry & Molecular Biology
Jiao Zhao, Jeremy Esque, Isabelle Andre, Michael J. O'Donohue, Regis Faure
Summary: The GH-51 alpha-L-arabinofuranosidase from Thermobacillus xylanilyticus exhibits versatile catalytic properties, with mutants showing increased yields and regioselectivity in the synthesis of furanobiosides. The study demonstrates the potential usefulness of these mutants for glycosynthesis, particularly in the production of biologically-relevant glycoconjugates. Through in-depth characterization, it was found that mutants can maximize the yield of homo-disaccharides by using higher substrate concentrations.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chiho Terada, Sho Usuki, Kazuya Nakata
Summary: TiO2 photocatalytic reaction is an environmentally friendly and promising method to convert biomass-derived compounds into rare sugars. In this study, d-sorbitol was treated with a TiO2 photocatalyst under light irradiation, and various rare sugars were produced. The production of these rare sugars was confirmed through analytical techniques such as high-performance liquid chromatography and proton nuclear magnetic resonance spectroscopy.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Organic
Lukas Fliegel, Jens Christoffers
Summary: Reacting beta-oxoesters with PIFA yields alpha-(iodophenyl) derivatives, which serve as starting materials for the preparation of [b] annulated benzofurane derivatives through copper-catalyzed C-O coupling reaction. The resulting scaffold shows great potential in medicinal chemistry and can be diversified to obtain various structurally different compounds.
Article
Chemistry, Physical
F. V. Pishchugin, I. T. Tuleberdiev
Summary: The kinetics and mechanism of condensation and transaldimination reactions between pyridoxal and different alanine compounds were studied using UV spectroscopy and polarimetry. The results indicate that these reactions proceed through two stages, involving the formation of intermediate products with specific structures.
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Biochemistry & Molecular Biology
Eduardo Rosado, Paloma Delgado-Fernandez, Blanca de las Rivas, Rosario Munoz, Francisco Javier Moreno, Nieves Corzo, Cesar Mateo
Summary: This study presents the synthesis of beta-galactosyl xylitol derivatives using immobilized LacA beta-galactosidase from Lactobacillus plantarum WCFS1. The immobilized enzyme exhibited high activity and stability, allowing for the synthesis of a large amount of beta-galactosyl xylitol derivatives with improved efficiency. It also showed lower in vitro intestinal digestibility compared to lactose.
Article
Chemistry, Organic
Ansis Maleckis, Elwy H. Abdelkader, Iresha D. Herath, Gottfried Otting
Summary: Efficient syntheses of fluorinated leucines, valines, and alanines are described in this study. The synthetic routes provide rapid access to various isotopologues using readily available and inexpensive reagents. The fluorinated leucines and valines were found to be good substrates for cell-free protein expression, with particularly high incorporation yields and clean F-19-NMR spectra observed for valine residues synthesized with a single fluorine replacing a hydrogen stereospecifically.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Akihiro Ishiwata, Kiyotaka Fujita, Shinya Fushinobu, Katsunori Tanaka, Yukishige Ito
Summary: Methyl beta-L-arabinofuranosyl-(1 -> 2)-, -(1 -> 3)-, and -(1 -> 5)-alpha-L-arabinofuranosides have been stereoselectively synthesized using the NAP-IAD method. The substrate specificity of HypBA1 and XeHypBA1 on the different disaccharide linkages was studied, showing that HypBA1 has lower activity on beta-(1 -> 5)-linked disaccharide and XeHypBA1 has higher specificity on beta-(1 -> 2)-linked disaccharide.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Jun Duan, Xiangfei Jia, Kun Cao, Zhen Gao
Summary: In this study, a beta-galactosidase gene was cloned and expressed in Escherichia coli. The enzyme showed high activity towards specific substrates and achieved high yield of galactosyl glycerol synthesis under unoptimized conditions.
BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Tyler J. Doyon, Prasanth Kumar, Sierra Thein, Maeve Kim, Abigail Stitgen, Abbigail M. Grieger, Cormac Madigan, Patrick H. Willoughby, Andrew R. Buller
Summary: Enzymes from secondary metabolic pathways show potential for the selective synthesis of bioactive molecules, but their practical application depends on the development of efficient systems. ObiH, an l-threonine transaldolase, demonstrated the ability to selectively synthesize diverse non-standard amino acids on a scalable whole cell platform. Results showed high initial selectivity of the catalyst and a decrease in diastereomeric ratio of products at high conversion.
Article
Biochemistry & Molecular Biology
Alexey G. Gerbst, Dmitry Z. Vinnitsky, Alexandra I. Tokatly, Andrey S. Dmitrenok, Vadim B. Krylov, Nadezhda E. Ustuzhanina, Nikolay E. Nifantiev
Summary: This study investigated the conformational behavior of α- and β-derivatives of glucuronic acid using NMR and quantum chemistry approaches. The introduction of sulfates had little effect on the conformation of α-linked disaccharides, while significant conformational changes were observed for β-derivatives.
Article
Chemistry, Multidisciplinary
Bingxue Liu, Deguang Liu, Xianle Rong, Xi Lu, Yao Fu, Qiang Liu
Summary: A ligand-controlled stereoselective C-alkyl glycosylation reaction was reported for the synthesis of 2-deoxy-beta-C-alkyl glycosides from readily available glycals and alkyl halides. The method exhibits broad substrate scope and excellent diastereoselectivity under very mild conditions. In addition, a stereodivergent synthesis of 2-deoxy-C-ribofuranosides was achieved using different chiral bisoxazoline ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Li-Hao Chang, Oliver Seitz
Summary: Nucleic acid-programmed reactions have applications in drug screening and nucleic acid diagnosis, and show potential for a RNA-sensitive prodrug approach. In this study, we demonstrate peptide-PNA conjugates undergo peptidyl transfer reactions on RNA templates and uncover high reactivity of certain PNA sequence motifs and combinations of cell-penetrating peptides in the absence of a template. The products of templated peptidyl transfer show activity on HeLa cells and HEK293 cells, and the presence of cysteine enhances bioactivity.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Agriculture, Multidisciplinary
Alistair T. Richardson, Tony K. McGhie, Sarah B. Cordiner, Teiarere T. H. Stephens, David S. Larsen, William A. Laing, Nigel B. Perry
Summary: The study found the distribution and seasonal variation of AA-2 beta G in apples and other crops, indicating its general role in the metabolism of AA.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Polymer Science
Hideto Tsuji, Masato Yamasaki, Yuki Arakawa
Summary: In this study, new enantiomeric stereo periodical copolymers of lactic acids were synthesized and a novel type of stereocomplex (SC) formation between these enantiomeric SPCPs was reported. The melting temperatures of SC crystallites of the blend were found to be between the alpha- and beta-forms of the homocrystallites, which is different from the results observed for enantiomeric poly(lactic acid) homopolymers. The findings suggest the possibility of widening the physical properties and biodegradation behavior of PLA-based materials through the synthesis and stereocomplexation of various types of SPCPs with different stereosequences.
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
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)