Studies on Reactions Relating to Carbohydrates and Polysaccharides. Xxiii. Synthesis and Properties of Hydroxy Alkylidene Glycols and Glycerols

Hibbert, Harold; Whelen, Myron S.

doi:10.1021/ja01385a034

Cited by 9 publications

(2 citation statements)

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“…Method is from ref. 42. An aqueous solution of KMnO 4 (32 g, 200 mmol in 300 ml) was added at the rate of ∼20 ml/min to 2‐vinyl‐1,3‐dioxolane (30 ml, 300 mmol) (compound 1) suspended in 200 ml of water in a 3‐necked 1‐L flask.…”

Section: Methodsmentioning

confidence: 99%

A single‐molecule force spectroscopy nanosensor for the identification of new antibiotics and antimalarials

et al. 2010

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An important goal of nanotechnology is the application of individual molecule handling techniques to the discovery of potential new therapeutic agents. Of particular interest is the search for new inhibitors of metabolic routes exclusive of human pathogens, such as the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway essential for the viability of most human pathogenic bacteria and of the malaria parasite. Using atomic force microscopy single-molecule force spectroscopy (SMFS), we have probed at the single-molecule level the interaction of 1-deoxy-D-xylulose 5-phosphate synthase (DXS), which catalyzes the first step of the MEP pathway, with its two substrates, pyruvate and glyceraldehyde-3-phosphate. The data obtained in this pioneering SMFS analysis of a bisubstrate enzymatic reaction illustrate the substrate sequentiality in DXS activity and allow for the calculation of catalytic parameters with single-molecule resolution. The DXS inhibitor fluoropyruvate has been detected in our SMFS competition experiments at a concentration of 10 μM, improving by 2 orders of magnitude the sensitivity of conventional enzyme activity assays. The binding of DXS to pyruvate is a 2-step process with dissociation constants of k(off) = 6.1 × 10(-4) ± 7.5 × 10(-3) and 1.3 × 10(-2) ± 1.0 × 10(-2) s(-1), and reaction lengths of x(β) = 3.98 ± 0.33 and 0.52 ± 0.23 Å. These results constitute the first quantitative report on the use of nanotechnology for the biodiscovery of new antimalarial enzyme inhibitors and open the field for the identification of compounds represented only by a few dozens of molecules in the sensor chamber.

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Section: Methodsmentioning

confidence: 99%

A single‐molecule force spectroscopy nanosensor for the identification of new antibiotics and antimalarials

et al. 2010

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“…Owing to the large excess of glycerol, the reaction for GLAD and DHA could be driven nearly to completion. Impurity 3 (CAS# 112401-29-3) has only been reported by Hibbert and Whelen [ 40 ] and Fisher and Smith [ 41 ], but it was first reported to result from the storage of glycerol in our study. Impurity 4 has not been reported previously in the literature.…”

Section: Resultsmentioning

confidence: 57%

Effects of polyol excipient stability during storage and use on the quality of biopharmaceutical formulations

Sun

Liao

Jing

et al. 2022

Journal of Pharmaceutical Analysis

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Acroleindiethylacetal: Reaction with free radicals and copolymerization

Sastre¹,

Mateo²,

Acosta³

1978

Angew. Makromol. Chem.

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The reaction between acroleindiethylacetal (3.3diethoxypropene) and free radicals and the behaviour of this acetal in the free radical copolymerization with unsaturated monomers has been investigated. The decomposition of benzoyl peroxide and tert.-butyl peroxide in acroleindiethylacetal has been studied in the liquid phase. On the basis of the obtained products a mechanism is proposed which involves the abstraction of a hydrogen atom by a primary radical from a carbon atom which is adjacent to oxygen.We also tried to copolymerize the acetal with several conventional comonomers but copolymers were only obtained when acrylonitrile and maleic anhydride were used.The remarkably uniform composition of the copolymers from the acetal and maleic anhydride is explained through a donor-acceptor complex between the two monomers. ZUSAMMENFASSUNG:Die Reaktion zwischen Acroleindifthylacetal und Radikalen sowie das Verhalten dieses Acetals bei der radikalischen Copolymerisation mit ungesattigten Monomeren wurde untersucht. Auf Grund der Ergebnisse wird ein Mechanismus vorgeschlagen, der die Abstraktion eines H-Atoms von einem dem Sauerstoff benachbarten C-Atom durch ein Radikal beinhaltet. Copolymerisationsveruche des Acetals mit verschiedenen Monomeren waren nur mit Acrylnitril und Maleinsiiureanhydrid erfolgreich. Die bemerkenswert einheitliche Zusammensetzung des Acetal-Maleinsfureanhydrid-Copolymeren zeigt, daa die Reaktion uber einen Donor-Akzeptor-Komplex verlauft.

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Studies on Reactions Relating to Carbohydrates and Polysaccharides. Xxiii. Synthesis and Properties of Hydroxy Alkylidene Glycols and Glycerols

Cited by 9 publications

References 0 publications

A single‐molecule force spectroscopy nanosensor for the identification of new antibiotics and antimalarials

A single‐molecule force spectroscopy nanosensor for the identification of new antibiotics and antimalarials

Effects of polyol excipient stability during storage and use on the quality of biopharmaceutical formulations

Acroleindiethylacetal: Reaction with free radicals and copolymerization

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