Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

Chen, Zhaohang; Zhou, Pengcheng; Guo, Yuanxia; Anna, Anna; Bai, Jiakun; Qiao, Renzhong; Li, Chao

doi:10.1021/acs.joc.1c02573

Cited by 7 publications

(9 citation statements)

References 46 publications

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“…Molecular structure of substrates for the asymmetric aldol reaction, the self-aldol reaction, hydrogelators ( OC-13 to OC-24 ), and their self-assembled hydrogel networks that catalyzed the aldol reactions are shown. The SEM or TEM micrographs of the hydrogel network were adopted with permission from ref (copyright 2009 Royal Society of Chemistry), ref (copyright 2022 American Chemical Society), ref (copyright 2016 Wiley-VCH Verlag GmbH & Co. KGaA), ref (copyright 2021 Royal Society of Chemistry), and ref (copyright 2020 American Chemical Society).…”

Section: Introductionmentioning

confidence: 99%

“…It is worth noting that the proline-catalyzed aldol reaction in pure water (catalysis in solution phase) resulted in a poor yield (25%) but excellent enantioselectivity (99% ee) . On a similar note, recently Chen et al employed a guanosine-based hydrogel to catalyze the aldol reaction in water. Through a heating–cooling cycle, a transparent hydrogel was obtained via the self-assembly of guanosine, and a proline-functionalized boronic acid derivative ( OC-14 , Figure ) provided G quartets in buffered solution, which was further stabilized by K + ions.…”

Section: Introductionmentioning

confidence: 99%

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Chemical Transformations in Supramolecular Hydrogels

Das

Maity

2023

ACS Catal.

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Time and again, nature utilizes the available building blocks for the preparation of molecules and ordered architectures for vital processes such as cell motility and intercellular transport. As biological catalyst, enzymes allow these chemical transformations at their active sites with high efficiency and selectivity. Importantly, these chemical transformations take place in aqueous media. To mimic the activity of natural enzymes, control over the reactivity of reactants (or intermediates) is necessary for artificial catalytic systems in aqueous media. Altering the selectivity of aqueous chemical reactions could be feasible with an organized and confined media in which reactants or intermediates would possess specific orientations, similar to active sites of an enzyme. Supramolecular hydrogels could be such organized media, where the fibrillar hydrogel network can provide active surface area with efficient diffusion properties. Herein, we summarize the use of supramolecular hydrogels in catalysis and as nanoreactors for efficient chemical transformations in aqueous media. The advantages of carrying out reactions in supramolecular hydrogels and key factors for hydrogel-phase catalysis are discussed. Overall, characteristics of supramolecular hydrogels and molecular engineering over the catalytic microenvironment within a hydrogel are key in the development of efficient chemical transformations with selectivity. However, this field is its infancy, as there is a limited set of chemical transformations resembling enzymatic activity. Based on recent developments in this field, we expect a promising future for cleverly designed chemical transformations in supramolecular hydrogels and encourage applications in biological systems and the pharmaceutical industry.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical Transformations in Supramolecular Hydrogels

Das

Maity

2023

ACS Catal.

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“…7−9 Bioinspired nucleoside guanosine-derived hydrogels are well established in the literature. 10,11 Davis and co-workers reported guanosine boronic acid cross-linked ion selective G-quadruplex (G4) hydrogel where the role of metal ions on the stability was illustrated. 12 Additionally, they explained the stability of G4 in the presence of anion and organic dye molecule.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The functionalization of the nucleobases with the amino acid generates a new class of nucleobase amino acid conjugate analogs with unique properties. The H-bonding capability of nucleobase makes them an attractive choice in the field of heterocyclic chemistry and biomedicine. − Bioinspired nucleoside guanosine-derived hydrogels are well established in the literature. , Davis and co-workers reported guanosine boronic acid cross-linked ion selective G-quadruplex (G4) hydrogel where the role of metal ions on the stability was illustrated . Additionally, they explained the stability of G4 in the presence of anion and organic dye molecule .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Studies of Nucleobase Functionalized Hydrogels for Controlled Release of Vitamins

Bhowmik,

Ghosh,

Sanghvi

et al. 2023

ACS Appl. Bio Mater.

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The development of biomolecule-derived biocompatible scaffolds for drug delivery applications is an emerging research area. Herein, we have synthesized a series of nucleobase guanine (G) functionalized amino acid conjugates having different chain lengths to study their molecular self-assembly in the hydrogel state. The gelation properties have been induced by the correct choice of chain lengths of fatty acids present in nucleobase functionalized molecules. The effect of alkali metal cations, pH, and the concentration of nucleobase functionalized amino acid conjugates in the molecular self-assembly process has been explored. The presence of Hoogsteen hydrogen bonding interaction drives the formation of a G-quadruplex functionalized hydrogel. The DOSY nuclear magnetic resonance is also performed to evaluate the self-assembling behavior of the newly formed nucleobase functionalized hydrogel. The nanofibrillar morphology is responsible for the formation of a hydrogel, which has been confirmed by various microscopic experiments. The mechanical behaviors of the hydrogel were evaluated by rheological experiments. The in vitro biostability of the synthesized nucleobase amino acid conjugate is also investigated in the presence of hydrolytic enzymes proteinase K and chymotrypsin. Finally, the nucleobase functionalized hydrogel has been used as a drug delivery platform for the control and sustained pH-responsive release of vitamins B2 and B12. This synthesized nucleobase functionalized hydrogel also exhibits noncytotoxic behavior, which has been evaluated by their in vitro cell viability experiment using HEK 293 and MCF-7 cell lines.

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“…11–15 Of particular interest, guanosine and its derivatives can self-associate via hydrogen bonding to form G-quartet like polymeric assembly leading to the formation of programmable hydrogels. 16,17 Such nucleic acid hydrogels have been utilized as innovative platform for facilitating chemical reactions, 18–20 drug delivery, 21 antimicrobial effects etc . 22…”

mentioning

confidence: 99%