Complete Deracemization of Proteinogenic Glutamic Acid Using Viedma Ripening on a Metastable Conglomerate

Spix, Laura; Meekes, Hugo; Blaauw, Richard H.; Enckevort, W.J.P. van; Vlieg, E.

doi:10.1021/cg301343a

Cited by 52 publications

(67 citation statements)

References 22 publications

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“…As imilar situation was previously reported by Spix et al,w ho deracemized am etastable conglomerate of glutamic acid using Viedma ripening. [29] Racemization study Xenon,m ercury,d euteriuma nd LED lamps were tested as potentiall ight sourcesf or the racemization. Among them,t he xenon UV lamp provedt ob et he best solution,h aving ab road emission band covering both UV and visible regions.…”

Section: Conglomerate Screeningmentioning

confidence: 99%

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Belletti

Tortora

Mellema³

et al. 2019

Chemistry A European J

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Viedma ripening is ad eracemizationp rocess that has been used to deracemize ar ange of chiral molecules. The method hast wo major requirements:t he compound needs to crystallize as ac onglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of racemization methods is still ratherl imited. To extend the scope of Viedma ripening, in the present research we applied UV-light-induced racemization in a Viedmar ipening process, and report the successful deracemizationo faB INOL derivative crystallizing as ac onglomerate. Irradiation by UV light activatest he target compound in combination with an organic base, required to promote the excited-state proton transfer (ESPT), leadingt hereaftert o racemization. This offers an ew tool towards the development of Viedma ripening processes, by using ac heap and "green"c atalytic source like UV light to racemize suitable chiral compounds.

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Section: Conglomerate Screeningmentioning

confidence: 99%

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Belletti

Tortora

Mellema³

et al. 2019

Chemistry A European J

Self Cite

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“…Viedma ripening was first demonstrated for sodium chlorate, an intrinsically achiral compound that crystallizes as conglomerate crystals, but has since then been modified to work also for intrinsically chiral compounds e.g. amino acids [4][5][6][7] and pharmaceuticals [8][9][10] that crystallize as conglomerate crystals by incorporating a fast racemization reaction. The outcome of the deracemization process depends on the initial conditions 11,12 : mass or crystal size distribution (CSD) imbalance between the enantiomers 1,[13][14][15] , presence of chiral impurities 16 or additives [17][18][19] or circularly polarized light 20 .…”

Section: Introductionmentioning

confidence: 99%

Coupling Viedma Ripening with Racemic Crystal Transformations: Mechanism of Deracemization

Xiouras

Horst

Gerven

et al. 2017

Crystal Growth & Design

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It has been recently observed that coupling Viedma ripening with a seeded in-situ metastable racemic crystal to conglomerate transformation leads to accelerated and complete deracemization: crystal transformation-enhanced deracemization. By means of a simple kinetic model, we show that the mechanistic pathway of this new process depends profoundly on the interplay between the crystal transformation and racemization processes, which in turn influence the nucleation process of the counter enantiomer. If the nucleation of the counter enantiomer is suppressed (e.g. by sufficiently fast racemization, low amount of racemic compound or gradual feed, low relative solubility between racemic compound and conglomerate), deracemization proceeds via a second order asymmetric transformation (SOAT) and is limited primarily by the dissolution rate of the racemic crystals and the growth rate of the preferred enantiomer crystals. Breakage and agglomeration accelerate the process, but contrary to conventional Viedma ripening, they are not essential ingredients to explain the observed enantiomeric enrichment. If the nucleation process of the counter enantiomer is not sufficiently suppressed, deracemization is initially controlled by the dissolution rate of the racemic crystals, but Viedma ripening is subsequently required to convert the conglomerate crystals of the counter enantiomer formed by nucleation, resulting in slower deracemization kinetics. In both cases, the combined process leads to faster deracemization kinetics compared to conventional Viedma ripening, while it autocorrects for the main disadvantage of SOAT, i.e. the accidental nucleation of the counter enantiomer. In addition, crystal transformation-enhanced deracemization extends the range of applicability of solid-state deracemization processes to compounds that form metastable racemic crystals. interplay between the crystal transformation and racemization processes, which in turn influence the nucleation process of the counter enantiomer. If the nucleation of the counter enantiomer is 3 suppressed (e.g. by sufficiently fast racemization, low amount of racemic compound or gradual feed, low relative solubility between racemic compound and conglomerate), deracemization proceeds via a second order asymmetric transformation (SOAT) and is limited primarily by the dissolution rate of the racemic crystals and the growth rate of the preferred enantiomer crystals.Breakage and agglomeration accelerate the process, but contrary to conventional Viedma ripening, they are not essential ingredients to explain the observed enantiomeric enrichment. If the nucleation process of the counter enantiomer is not sufficiently suppressed, deracemization is initially controlled by the dissolution rate of the racemic crystals, but Viedma ripening is subsequently required to convert the conglomerate crystals of the counter enantiomer formed by nucleation, resulting in slower deracemization kinetics. In both cases, the combined process leads to faster deracemization kinetics compared ...

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“…The deracemisation of a metastable conglomerate of glutaric acid has been reported [90]. The deracemisation of a metastable conglomerate of glutaric acid has been reported [90].…”

Section: Discussionmentioning

confidence: 99%

Advances in Organic Crystal Chemistry

Tamura¹,

Miyata²

2015

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Complete Deracemization of Proteinogenic Glutamic Acid Using Viedma Ripening on a Metastable Conglomerate

Cited by 52 publications

References 22 publications

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Coupling Viedma Ripening with Racemic Crystal Transformations: Mechanism of Deracemization

Advances in Organic Crystal Chemistry

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