Ethanol-free antisolvent crystallization of glycine by liquefied dimethyl ether

Kanda, Hideki; Katsube, Tsubasa; Hoshino, Rintaro; Kishino, Mitsuhiro; Diono, Wahyu; Goto, Motonobu

doi:10.1016/j.heliyon.2020.e05258

Cited by 12 publications

(5 citation statements)

References 37 publications

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“…Nonphotochemical laser-induced nucleation (NPLIN), [162,[175][176][177][178][179][180][181] and crystallization in electromagnetic fields [182][183][184] have been taken as demonstration of the validity of such a model for the crystallization occurring in supersaturated (and aged) aqueous glycine solutions. The techniques based on changing the rate of increasing supersaturation (antisolvent crystallization, [185][186][187] spray-drying, [188][189][190][191][192] freeze-drying, [193][194][195][196][197] cooling at variable rates [45,198,199] ) suppose using the Ostwald's rule of stages, [200,201] when a metastable form nucleates first and in this way also the batch product can be prepared as a metastable polymorph. At the same time, many studies showed, that the relative rates of the growth of the already formed nuclei, and / or their solvent assistant transformation into other polymorphs are at least equally important.…”

Section: Crystallization Procedures and Mechanismsmentioning

confidence: 99%

Glycine: The Gift that Keeps on Giving

Boldyreva

2021

Israel Journal of Chemistry

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Glycine is a small molecule. It cannot change its conformation and is achiral. Despite the apparent simplicity, glycine shows endless diversity in its behavior over many phenomena. It was the first amino acid for which polymorphism was reported, first on crystallization and then on hydrostatic compression. The polymorphs differ in their physical properties and their biological activity. Glycine clusters persist in solution, leading to "solution memory". Phenomena at interfaces are critically important for crystal growth, dissolution, and for physical properties, which can be at times unexpected, like polarity in centrosymmetric αpolymorph. It is a great pleasure to remind of these remarkable phenomena in a special issue honoring professors Meir Lahav and Leslie Leiserowitz, who pioneered the study of the behavior of this unique molecule in many respects, and showed how complex and non-trivial phenomena can be at interfaces: between phases and between research fields.

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Section: Crystallization Procedures and Mechanismsmentioning

confidence: 99%

Glycine: The Gift that Keeps on Giving

Boldyreva

2021

Israel Journal of Chemistry

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“…The luminescence intensity of the DME-treated samples was higher than that of the original sample. Since DME has the ability to cleave hydrogen bonds, 47 it is possible that DME cleaves the hydrogen bonds between the phosphate groups of the DNA and the surrounding polar material, leaving the phosphate groups of the DNA free to more easily bind to the fluorescent dye. When treated with DNase for 1 day after DME extraction, no DNA was detected, revealing a complete degradation to <100 bp, as shown in (c).…”

Section: ■ Introductionmentioning

confidence: 99%

Surfactant-Free Decellularization of Porcine Aortic Tissue by Subcritical Dimethyl Ether

et al. 2021

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Porcine aortic tissue was decellularized by subcritical dimethyl ether (DME) used as an alternative to the surfactant sodium dodecyl sulfate. The process included three steps. For the first step, lipids were extracted from the porcine aorta using subcritical DME at 23 °C with a DME pressure of 0.56 MPa. Next, DME was evaporated from the aorta under atmospheric pressure and temperature. The second step involved DNA fragmentation by DNase, which was primarily identical to the common method. For the third step, similar to the common method, DNA fragments were removed by washing with water and ethanol. After 3 days of DNase treatment, the amount of DNA remaining in the porcine aorta was 40 ng/dry-mg, which was lower than the standard value of 50 ng/mg-dry. Hematoxylin and eosin staining showed that most cell nuclei were removed from the aorta. These results demonstrate that subcritical DME eliminates the need to utilize surfactants.

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“…On the other hand, the formation of crystals was tracked with the turbidity meter, indicating the beginning of the time crystallization is initiated. Glycine-ethanol-water was the model crystallizing system chosen for this study as it gives a neutral pH environment for the crystallization (so it cancels out the impact of pH) and has been generally used as a model molecule for antisolvent crystallization [ 30 ]. The variation of operating conditions is summarized in Table 2 .…”

Section: Methodsmentioning

confidence: 99%

Key Parameters Impacting the Crystal Formation in Antisolvent Membrane-Assisted Crystallization

et al. 2023

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Antisolvent crystallization is commonly used in the formation of heat-sensitive compounds as it is the case for most active pharmaceutical ingredients. Membranes have the ability to control the antisolvent mass transfer to the reaction medium, providing excellent mixing that inhibits the formation of local supersaturations responsible for the undesired properties of the resulting crystals. Still, optimization of the operating conditions is required. This work investigates the impact of solution velocity, the effect of antisolvent composition, the temperature and gravity, using glycine-water-ethanol as a model crystallization system, and polypropylene flat sheet membranes. Results proved that in any condition, membranes were consistent in providing a narrow crystal size distribution (CSD) with coefficient of variation (CV) in the range of 0.5–0.6 as opposed to 0.7 obtained by batch and drop-by-drop crystallization. The prism-like shape of glycine crystals was maintained as well, but slightly altered when operating at a temperature of 35 °C with the appearance of smoother crystal edges. Finally, the mean crystal size was within 23 to 40 µm and did not necessarily follow a clear correlation with the solution velocities or antisolvent composition, but increased with the application of higher temperature or gravity resistance. Besides, the monoclinic form of α-glycine was perfectly maintained in all conditions. The results at each condition correlated directly with the antisolvent transmembrane flux that ranged between 0.0002 and 0.001 kg/m2. s. In conclusion, membrane antisolvent crystallization is a robust solution offering consistent crystal properties under optimal operating conditions.

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Ethanol-free antisolvent crystallization of glycine by liquefied dimethyl ether

Cited by 12 publications

References 37 publications

Glycine: The Gift that Keeps on Giving

Glycine: The Gift that Keeps on Giving

Surfactant-Free Decellularization of Porcine Aortic Tissue by Subcritical Dimethyl Ether

Key Parameters Impacting the Crystal Formation in Antisolvent Membrane-Assisted Crystallization

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