Sulfur oxidation in supercritical carbon dioxide: dramatic pressure dependant enhancement of diastereoselectivity for sulfoxidation of cysteine derivatives

Oakes, R. Scott; Clifford, Anthony A.; Bartle, Keith D.; Pett, Mark Thornton; Rayner, Christopher M.

doi:10.1039/a809434i

Cited by 44 publications

(5 citation statements)

References 9 publications

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“…Oakes et al reported exclusive pressure optimized diastereo-selectivity achieved via use of SCF drying at~110 bar of carbon dioxide in the asymmetric catalytic sulfoxidation of cysteine and methionine. A diastereomeric purity of~95% was obtained by this method, which could not be achieved by using conventional solvents [60].…”

Section: Form Control and Polymorphismmentioning

confidence: 90%

Using Supercritical Fluid Technology as a Green Alternative During the Preparation of Drug Delivery Systems

Chakravarty¹,

Famili²,

Nagapudi³

et al. 2019

Pharmaceutics

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Micro- and nano-carrier formulations have been developed as drug delivery systems for active pharmaceutical ingredients (APIs) that suffer from poor physico-chemical, pharmacokinetic, and pharmacodynamic properties. Encapsulating the APIs in such systems can help improve their stability by protecting them from harsh conditions such as light, oxygen, temperature, pH, enzymes, and others. Consequently, the API’s dissolution rate and bioavailability are tremendously improved. Conventional techniques used in the production of these drug carrier formulations have several drawbacks, including thermal and chemical stability of the APIs, excessive use of organic solvents, high residual solvent levels, difficult particle size control and distributions, drug loading-related challenges, and time and energy consumption. This review illustrates how supercritical fluid (SCF) technologies can be superior in controlling the morphology of API particles and in the production of drug carriers due to SCF’s non-toxic, inert, economical, and environmentally friendly properties. The SCF’s advantages, benefits, and various preparation methods are discussed. Drug carrier formulations discussed in this review include microparticles, nanoparticles, polymeric membranes, aerogels, microporous foams, solid lipid nanoparticles, and liposomes.

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Section: Form Control and Polymorphismmentioning

confidence: 90%

Using Supercritical Fluid Technology as a Green Alternative During the Preparation of Drug Delivery Systems

Chakravarty¹,

Famili²,

Nagapudi³

et al. 2019

Pharmaceutics

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“…When increasing the pressure, the surplus of diastereomers increases up to a maximum of > 95 % at 185 bar (40°C). With further increase in pressure, the surplus decreases again to a value of about 30 %, remaining more or less constant above 300 bar [110,111].…”

Section: Oxidations (For Surveys See [19 92-96])mentioning

confidence: 91%

Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide

Kruse

Vogel

2007

Chem Eng & Technol

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Dedicated to Prof. Dr.-Ing. Jens Weitkamp on the occasion of his 65th birthdayOver the past few years, supercritical fluids have received considerable interest as reaction media. Supercritical fluids combine properties of gases and liquids. Densities are lower than in the liquid phase, but significantly higher than in the gas phase. This makes supercritical fluids excellent solvents for a variety of substances. The good dissolution capacity exists only in or near the supercritical range. Reaction products can be separated, for instance, simply by decreasing temperature and pressure. This may be used to intensify the process as complex separation processes, like distillation, are avoided.

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“…Rayner et al ont e ´tudie ´la diaste ´re ´ose ´lectivite ´de l'oxydation asyme ´trique de la cyste ´ine en sulfoxydes correspondants [16] en optimisant la pression du fluide SC. Un exce `s diaste ´re ´ome ´rique de 95 % d.e a e ´te ´obtenu a 11 MPa de CO 2 (Fig.…”

Section: Re´action D'oxydationunclassified

Applications du CO2 supercritique en synthèse organique et obtention de molécules organiques finement divisées

Mahboub

2011

Comptes Rendus. Chimie

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ce travail, nous pre ´sentons des re ´sultats concernant les diffe ´rentes applications du gaz carbonique (CO 2 ) supercritique dans la synthe `se organique et en pharmacologie. Nous indiquons e ´galement l'inte ´re ˆt d'obtenir des mole ´cules organiques finement divise ´es a l'aide de ce nouveau type de milieu re ´actionnel. ß 2010 Acade ´mie des sciences. Publie ´par Elsevier Masson SAS. Tous droits re ´serve ´s.

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Sulfur oxidation in supercritical carbon dioxide: dramatic pressure dependant enhancement of diastereoselectivity for sulfoxidation of cysteine derivatives

Cited by 44 publications

References 9 publications

Using Supercritical Fluid Technology as a Green Alternative During the Preparation of Drug Delivery Systems

Using Supercritical Fluid Technology as a Green Alternative During the Preparation of Drug Delivery Systems

Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide

Applications du CO2 supercritique en synthèse organique et obtention de molécules organiques finement divisées

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