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Binding Between Cyclohexanohemicucurbit[n]urils and Polar Organic Guests.

ABSTRACT: Inherently chiral, barrel-shaped, macrocyclic hosts such as cyclohexanohemicucurbit[n]urils (cycHC[n]) bind zinc porphyrins and trifluoroacetic acid externally in halogenated solvents. In the current study, we tested a set of eighteen organic guests with various functional groups and polarity, namely, thiophenols, phenols, and carboxylic and sulfonic acids, to identify a preference toward hydrogen bond-donating molecules for homologous cycHC[6] and cycHC[8]. Guests were characterized by Hirshfeld partial charges on acidic hydrogens and their binding by ¹H and ¹⁹F NMR titrations. Evaluation of association constants revealed the complexity of the system and indirectly proved an external binding with stoichiometry over 2:1 for both homologs. It was found that overall binding strength is influenced by the stoichiometry of the formed complexes, the partial atomic charge on the hydrogen atom of the hydrogen bond donor, and the bulkiness of the guest. Additionally, a study on the formation of complexes with halogen anions (Cl^- and Br^-) in methanol and chloroform, analyzed by ¹H NMR, did not confirm complexation. The current study widens the scope of potential applications for host molecules by demonstrating the formation of hydrogen-bonded complexes with multisite hydrogen bond acceptors such as cycHC[6] and cycHC[8].

SUBMITTER: Ustrnul L

PROVIDER: S-EPMC8273652 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Organic matter recycling in marine systems is largely driven by microbial processes, particularly in the Arctic where primary production and inputs can be temporally offset from upper trophic level consumption. This study followed bacterial dynamics in the chlorophyll maximum of the Bering Strait and sediment-water interface of the Chukchi Sea using metaproteomic and 16S rRNA methods to measure cellular function and taxonomic composition under low and high marine-derived particulate organic matter (POM) treatments at 0°C. Parallel analysis of major organic components (lipids and amino acids) allowed a comparison of microbial-POM interactions. Over the 10 day experimental period, bacteria under both treatments showed rapid community responses and changes in proteomic expression, accompanied by small changes in the concentration and distributions of organic components. In the Bering Strait community, protein translation was an important immediate cellular response under both POM scenarios while specific metabolic processes were more distinct between treatments. For example, under both conditions, evidence for carboxylic acid metabolism increased at day 6 while carbohydrate utilization as an energy source showed unique patterns as the experiments progressed. With POM additions to the Bering Strait community, nitrogen transport and regulation went up, including nitrogen fixation and ammonia assimilation, by day 6. In addition, a number of vitamin enzymatic cofactors were enriched by this day, providing evidence for an increase in C1 metabolism at that time. Low POM conditions stimulated the cycling and synthesis of amino acids, which was not as pronounced under the high POM treatment. In the Chukchi Sea community, nitrate reduction and substrate-specific transporter activity was statistically higher than in the Bering Strait, especially under low POM conditions. Taxonomic inference revealed that a wide range of bacterial classes were associated with the shifting cellular functions, but that Alphaproteobacteria, Gammaproteobacteria and Flavobacteria controlled most of these protein abundances. Activities of all classes were highly variable, with less dominant bacterial groups exhibiting a particularly strong degree of niche separation.

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Binding Between Cyclohexanohemicucurbit[n]urils and Polar Organic Guests.

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