The formation of thymidine-based T-tetramers with remarkable structural and metal ion size effects

Luo, Qun; Wu, Dayong; Liu, Shixiong; Tang, Daihua; Huang, Yong; Liu, Xinhou; Wang, Fuyi; Wang, Ruiyao; Wu, Gang

doi:10.1039/c0ob00520g

Cited by 10 publications

(6 citation statements)

References 40 publications

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“…Despite numerous reports on C−S bond formation, the tert ‐butyl nitrite has been found to be quite useful for the heterocyclization reaction [111–114] . Saritha and her group demonstrated that when tert ‐butyl nitrite is supported by ascorbic acid and iodine in DMSO, it leads to sulfenylpolycyclic aromatics/heteroaromatics starting from pyrazole amine.…”

Section: C−s Bond Formationmentioning

confidence: 99%

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

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Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis of the use of iodine and DMSO in various synthetic routes for the preparation of valuable targets are presented. These methods reduce the acceptance on expensive additives and reagents, and offer a more sustainable solution for the synthesis of these important chemical scaffolds.

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Section: C−s Bond Formationmentioning

confidence: 99%

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

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show abstract

“…the metal ions serving as the template centers of the ligands or subunits and stabilizing the MNCs through ion-dipole interactions, especially when the ligands or subunits are nucleobases [7,8] and nucleosides. [9][10][11] However, if one considers about the types of template centers in MNCs formed in the gas phase and in self-assemblies formed in the solution phase, the available template ions should not be limited to just metal ions. Actually, organic cations can be capsuled in the nanospace of many self-assemblies.…”

Section: Introductionmentioning

confidence: 99%

Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations

et al. 2014

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As the novel magic number clusters of nucleobases, the thymine quintets induced by ammonium ion (NH4(+)), and particularly by its derivatives such as protonated alkyl amines and protonated aryl amines, have been studied by electrospray ionization mass spectrometry (ESI-MS) and density functional theory (DFT) calculations. The DFT-optimized geometry of NH4(+) induced thymine quintet ([T5 + NH4](+)) reveals some new features including three additional hydrogen bonds between NH4(+) and its surrounding thymine molecules when compared with that of the alkali metal ions induced thymine quintets. In addition, the fourth hydrogen atom of NH4(+) is sticking out the assembly, and, thus, it might be replaced by an organic group R to form the protonated primary amine induced thymine quintet ([T5 + R - NH3](+)), a hypothesis that has been confirmed by both DFT calculations and ESI-MS experiments. Furthermore, the relative abilities of the different protonated primary amines for inducing the thymine quintets are investigated by ESI-MS competition experiments, and the results have shown a clear trend of stronger ability as the alkyl chain gets longer or as the aryl ring gets larger for the alkyl amines or the aryl amines. Two basic influence factors are consequently identified: one is the ability of the alkyl amine to accept proton, another is the π-π stacking interaction between the aryl ring and the π-surface of the thymine molecule(s), whose explanations are strongly supported by multiple types of thermochemical data, various control experiments and DFT calculations.

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“…To date, only a limited number of enzymes responsible for assembling PhGs have been documented, facilitating the biosynthesis of compounds like verbascoside and ligupurpuroside B [24–29] . These include UGT85AF8, a tyrosol glucosyltransferase (GT); [25] UGT79G7, an osmanthuside A 1,3‐rhamnosyltransferase; [25] UGT79 A19, an osmanthuside B 1,4‐rhamnosyltransferase; [25] and SiAT1, a salidroside hydroxycinnamoyltransferase [24] (Table 1).…”

Section: Introductionmentioning

confidence: 99%

Construct Phenylethanoid Glycosides Harnessing Biosynthetic Networks, Protein Engineering and One‐Pot Multienzyme Cascades

Yao,

Wang,

Wang

et al. 2024

Angew Chem Int Ed

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Phenylethanoid glycosides (PhGs) exhibit a multitude of structural variations linked to diverse pharmacological activities. Assembling various PhGs via multienzyme cascades represents a concise strategy over traditional synthetic methods. However, the challenge lies in identifying a comprehensive set of catalytic enzymes. This study explores biosynthetic PhG reconstruction from natural precursors, aiming to replicate and amplify their structural diversity. We discovered 12 catalytic enzymes, including four novel 6'‐OH glycosyltransferases and three new polyphenol oxidases, revealing the intricate network in PhG biosynthesis. Subsequently, the crystal structure of CmGT3 (2.62 Å) was obtained, guiding the identification of conserved residue 144# as a critical determinant for sugar donor specificity. Engineering this residue in PhG glycosyltransferases (FsGT61, CmGT3, and FsGT6) altered their sugar donor recognition. Finally, a one‐pot multienzyme cascade was established, where the combined action of glycosyltransferases and acyltransferases boosted conversion rates by up to 12.6‐fold. This cascade facilitated the reconstruction of 26 PhGs with conversion rates ranging from 5‐100%, and 20 additional PhGs detectable by mass spectrometry. PhGs with extra glycosyl and hydroxyl modules demonstrated notable liver cell protection. This work not only provides catalytic tools for PhGs biosynthesis, but also serves as a proof‐of‐concept for cell‐free enzymatic construction of diverse natural products.

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The formation of thymidine-based T-tetramers with remarkable structural and metal ion size effects

Cited by 10 publications

References 40 publications

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Protonated primary amines induced thymine quintets studied by electrospray ionization mass spectrometry and density functional theory calculations

Construct Phenylethanoid Glycosides Harnessing Biosynthetic Networks, Protein Engineering and One‐Pot Multienzyme Cascades

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