NMR Spectroscopic Studies on Complex Formation between Dimeric (R)-3-Hydroxybutanoic Acid and β-Cyclodextrin

doi:10.1246/BCSJ.71.1953

Paper

NMR Spectroscopic Studies on Complex Formation between Dimeric (R)-3-Hydroxybutanoic Acid and β-Cyclodextrin

Published Aug 15, 1998 · Jun Li, J. Uzawa, Y. Doi

Bulletin of the Chemical Society of Japan

Q2 SJR score

6

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Dimeric (R)-3-hydroxybutanoic acid (3HB) was found to form an inclusion complex selectively with β-cyclodextrin (β-CD) in aqueous solution. The complex formation was confirmed by the changes of 1H and 13C NMR spectra of both dimeric 3HB and β-CD in D2O solution. The continuous variation experiments showed the formation of a 1 : 1 inclusion complex. The dissociation constants at various temperatures between 15 and 47 °C were determined and the thermodynamic analysis of the complex formation was performed. The results indicated that the complex formation is enthalpically favorable but entropically unfavorable. We propose that the 3HB unit with carboxy end-group is located in the narrow side of the β-CD cavity.

Study Snapshot

Dimeric (R)-3-hydroxybutanoic acid forms an inclusion complex with -cyclodextrin in aqueous solution, with the carboxy end-group occupying the narrow side of the -CD cavity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

NMR Spectroscopic Studies on Complex Formation between Dimeric (R)-3-Hydroxybutanoic Acid and β-Cyclodextrin

Sign up to use Study Snapshot

References

Conformational Analysis of Oligomers of (R)-3-Hydroxybutanoic Acid in Solutions by 1H NMR Spectroscopy

In non-polar organic solvents, only the gauche conformer is predominant in (R)-3-hydroxybutanoic acid oligomers, with trans and gauche conformers preferring in solutions.

Conformational Behavior of Methyl (3R)-3-{[(3′R)-3′ -Hydroxybutanoyl]oxy}butanoate in Solutions: Effect of Intramolecular Hydrogen Bond

MHBOB exhibits conformational behavior similar to that of the P(3-HB) polymer backbone, with trans and gauche conformers predominant, while the hydroxy group adopts a more pronounced gauche conformation.

Poly-3-hydroxybutyrate/polyphosphate complexes form voltage-activated Ca2+ channels in the plasma membranes of Escherichia coli.

Poly-3-hydroxybutyrate/calcium polyphosphate complexes form voltage-activated calcium channels in Escherichia coli plasma membranes, suggesting they are evolutionary antecedents of protein calcium channels.

Inorganic Polyphosphates in the Acquisition of Competence in Escherichia coli(*)

The PHB-Ca2+-polyP complex in Escherichia coli membranes alters lipid conformation, allowing DNA entry by perturbing the lipid matrix's conformation.

Production of Polyhydroxyalkanoates, a Family of Biodegradable Plastics and Elastomers, in Bacteria and Plants

Polyhydroxyalkanoates (PHAs) are a promising source of biodegradable plastics and elastomers, with potential for large-scale production and cost-competitive production in crop plants.

Citations

Formation of [3]Pseudorotaxanes from β-cyclodextrin and a Series of Dicarboxylic Acids with Their Corresponding α, ω-alkanedicarboxylate Anions

The study reveals that -cyclodextrin and dicarboxylic acids can form [3]pseudorotaxane structures, with -CD arranged in dimers threaded onto one aliphatic chain, and the binding mode of 1:1 inclusion complex is excluded due

Cyclodextrin-based supramolecular architectures: syntheses, structures, and applications for drug and gene delivery.

Cyclodextrin-based supramolecular biomaterials show potential for controlled drug delivery and gene delivery, with reduced cytotoxicity compared to conventional polymeric materials.

Role of intermolecular interaction between hydrophobic blocks in block-selected inclusion complexation of amphiphilic poly(ethylene oxide)-poly[(R)-3-hydroxybutyrate]-poly(ethylene oxide) triblock copolymers with cyclodextrins

Higher temperature increases the hydrophobic interaction between hydrophobic blocks, leading to block-selected inclusion complexation of amphiphilic poly(ethylene oxide)-poly((R)-3-hydroxybutyrate)-poly(ethylene oxide) triblock copolymers with cyclodextrins.

Formation of inclusion complexes between dimers of (R)-3-hydroxybutanoic acid and β-cyclodextrin: thermodynamic study of the complexation and conformational analysis of the complexed dimers

The formation of inclusion complexes between (R)-3-hydroxybutanoic acid dimers and -cyclodextrin is enthalpically favorable but unfavorable due to hydrogen bonds and extended conformation of the complexed dimers.

Cyclodextrin-based self-assembled supramolecular hydrogels and cationic polyrotaxanes for drug and gene delivery applications

Cyclodextrin-based supramolecular hydrogels and cationic polyrotaxanes offer novel drug and gene delivery systems with low cytotoxicity, strong DNA-binding capability, and high gene transfection efficiency.