Highly efficient chiral resolution of DL-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions

TitleHighly efficient chiral resolution of DL-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions
Publication TypeJournal Article
Year of Publication2014
AuthorsIwama, S, Kuyama, K, Mori, Y, Manoj, K, Gonnade, RG, Suzuki, K, Hughes, CE, P. Williams, A, Harris, KDM, Veesler, S, Takahashi, H, Tsue, H, Tamura, R
JournalChemistry-A European Journal
Volume20
Issue33
Pagination10343-10350
Date PublishedAUG
ISSN0947-6539
KeywordsAmino acids, chiral resolution, cocrystals, Crystal growth, phase transitions
Abstract

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 (CNMR)-C-13 spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed.

DOI10.1002/chem.201402446
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.35

Divison category: 
Center for Material Characterization (CMC)