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Highly Efficient Chiral Resolution of dl-Arginine by Cocrystal Formation Followed by Recrystallization under Preferential-Enrichment Conditions

Iwama, Sekai ; Kuyama, Kazunori ; Mori, Yuko ; Manoj, Kochunnoonny ; Gonnade, Rajesh G. ; Suzuki, Katsuaki ; Hughes, Colan E. ; Williams, P. Andrew ; Harris, Kenneth D. M. ; Veesler, Stéphane ; Takahashi, Hiroki ; Tsue, Hirohito ; Tamura, Rui

Chemistry : a European journal, 2014-08, Vol.20 (33), p.10343-10350 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

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Título:
Highly Efficient Chiral Resolution of dl-Arginine by Cocrystal Formation Followed by Recrystallization under Preferential-Enrichment Conditions
Autor: Iwama, Sekai ; Kuyama, Kazunori ; Mori, Yuko ; Manoj, Kochunnoonny ; Gonnade, Rajesh G. ; Suzuki, Katsuaki ; Hughes, Colan E. ; Williams, P. Andrew ; Harris, Kenneth D. M. ; Veesler, Stéphane ; Takahashi, Hiroki ; Tsue, Hirohito ; Tamura, Rui
Assuntos: amino acids ; Arginine - chemistry ; Broken symmetry ; Chemistry ; chiral resolution ; cocrystals ; crystal growth ; Crystal structure ; Crystallization ; Crystallography, X-Ray ; Crystals ; Enrichment ; Eutectics ; Fumaric acid ; Models, Molecular ; Phase Transition ; Phase transitions ; Recrystallization ; Stereoisomerism
É parte de: Chemistry : a European journal, 2014-08, Vol.20 (33), p.10343-10350
Notas: JSPS - No. 23245008
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ArticleID:CHEM201402446
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: An excellent chiral symmetry‐breaking spontaneous enantiomeric resolution phenomenon, denoted preferential enrichment, was observed on recrystallization of the 1:1 cocrystal of dl‐arginine and fumaric acid, which is classified as a racemic compound crystal with a high eutectic ee value (>95 %), under non‐equilibrium crystallization conditions. On the basis of temperature‐controlled video microscopy and in situ time‐resolved solid‐state 13C NMR spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed. Chiral symmetry breaking: A spontaneous enantiomeric resolution phenomenon, denoted preferential enrichment (PE), was observed for the cocrystal of dl‐arginine and fumaric acid, which is a racemic compound crystal with a high eutectic ee value and a new type of crystal structure, under non‐equilibrium crystallization conditions (see figure). A direct phase transition of the molecular clusters in the supersaturated solution to uniform stable crystals also induced PE.
Editor: Weinheim: WILEY-VCH Verlag
Idioma: Inglês

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Highly Efficient Chiral Resolution of dl-Arginine by Cocrystal Formation Followed by Recrystallization under Preferential-Enrichment Conditions

Iwama, Sekai ; Kuyama, Kazunori ; Mori, Yuko ; Manoj, Kochunnoonny ; Gonnade, Rajesh G. ; Suzuki, Katsuaki ; Hughes, Colan E. ; Williams, P. Andrew ; Harris, Kenneth D. M. ; Veesler, Stéphane ; Takahashi, Hiroki ; Tsue, Hirohito ; Tamura, Rui

Weinheim: WILEY-VCH Verlag

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