Optical Resolution by Preferential Crystallization of (<i>RS</i>)-2-Amino-3-(2-carboxyethylthio)propanoic Acid

Shiraiwa, Tadashi; Kubo, Motoki; Watanabe, Mitsuhiro; Nakatani, Hidemasa; Ohkubo, Masanori; Kurokawa, Hidemoto

doi:10.1271/bbb.62.818

Cited by 8 publications

(6 citation statements)

References 1 publication

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“…6,7 On the other hand, a conglomerate can be resolved on a large scale by the preferential crystallization method (also known as direct crystallization), which involves introducing seed crystals of the desired enantiomer into a cooling saturated solution of the racemic mixture and harvesting the crystals that grow on the seeds. 4,8,9 The formation of different types of racemic mixtures is a result of the difference in the structure and energy between the homochiral and heterochiral crystals, which is the origin of chiral discrimination in the solid state. In view of significant differences in the melting behavior of racemic species, their thermodynamic properties must differ.…”

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confidence: 99%

Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride

Wang

Ching

2002

Chirality

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Characterization of the racemic species, which can be a racemic compound, a racemic conglomerate, or a pseudoracemate (solid solution), is a prerequisite for the design of crystallization resolution processes. It is useful to determine the solid/liquid equilibrium solubility of the enantiomer mixtures for crystallization operation. For the beta-blocker drug propranolol hydrochloride, Gibbs free energy of formation of racemic compound and entropy of mixing of the (R)- and (S)- enantiomers in the liquid state for racemic conglomerate were calculated. The structural differences between (R, S)-propranolol hydrochloride and its (S)-enantiomer were further investigated by powder X-ray diffraction patterns, infrared spectra, and solid-state NMR spectra. The solubility and metastable zone width of (R, S)- propranolol hydrochloride in a mixed solvent of methanol and acetone were determined by cooling crystallization over the temperature range 3.5-42.5 degrees C. The ternary solubility diagram of (R)-, (S)-propranolol hydrochloride was constructed using the same mixed solvent. The diagram will be useful as a guide for choosing crystallization operation conditions to produce pure enantiomers.

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confidence: 99%

Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride

Wang

Ching

2002

Chirality

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“…Prior to analysis, the main urinary metabolites of ACR, 3‐HPMA, and CEMA were chemically synthesized and used as authentic standards via Michael addition reactions of L ‐cysteine with respective allyl alcohol and acrylic acid followed by acetylation ( Figures 7 A,B). [ 37 ] Their structures were confirmed by NMR experiments and LC‐MS data. In brief, 3‐HPMA possessed an accurate molecular ion at m/z 220.0649 [M−H] − (fudosteine + Ac).…”

Section: Resultsmentioning

confidence: 88%

“…In a similar manner, CEMA owned an accurate molecular ion at m/z 234.0442 [M−H] − (CEC + Ac). The appearance of an extra singlet at 𝛿 1.99 (3H, s) in the 1 H-NMR spectra along with according carbon signals at 22.9 (q, -CH 3 ) and 172.8 (s, C = O) in the 13 C-NMR spectra, compared to S-(2-carboxyethyl)-Lcysteine (CEC), [37] revealed the structure of N-acetyl CEC, namely CEMA. Characteristic MS 2 fragments at m/z 105.0015 (corresponding to 3-mercaptopropanoic acid from the cleavage of C 3 -S bond) and m/z 162.0231 [M−acrylic acid−H] − agreed such a structural elucidation (Figure S4B, Supporting Information).…”

Section: Phloretin Administration Reduced the Urinary Excretion Of Ac...mentioning

confidence: 99%

Metabolic Investigation on the Interaction Mechanism between Dietary Dihydrochalcone Intake and Lipid Peroxidation Product Acrolein Reduction

Zhu

Wang

Huang

et al. 2022

Molecular Nutrition Food Res

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Scope Acrolein (ACR), a lipid peroxidation product, pathologically participates in various chronic diseases. In vitro evidence suggestes that dietary dihydrochalcones (DHCs) potentiate safe and alternative therapeutics to synthetic pharmaceuticals for ACR scavenging. Here, to investigate whether ingested DHCs could trap ACR and thereof result in reductions in endogenous ACR in mice is aimed. Methods and results Three doses of phloretin (25, 100, and 400 mg kg−1), a major dietary DHC, are orally administrated to mice and 24 h urine and fecal samples are collected, respectively. High‐resolution MS‐based targeted metabolomics reveal for the first time that phloretin and its oxidized metabolite are able to trap endogenous ACR via formation of ACR conjugates. Quantification further demonstrate that a) more than 13% of ingested phloretin can dose‐dependently trap 0.77−9.92 nmol of ACR within 24 h; b) phloretin ingestion leads to marked reductions in both free ACR and ACR metabolites in mouse urine compared to control; and c) trapping reactions by phloretin can account for up to 20.1% of the total decreases in endogenous ACR, depending on the administration doses. Conclusion Findings from this study indicate that regular consumption of DHCs‐rich diets holds great promise to alleviate the development of ACR‐associated chronic diseases.

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“…A significant number of research works have been published related to the chiral resolution of racemates on a large scale using kinetic resolution by crystallization and enzymatic resolution methods [26][27][28][29] . Liquid chromatography (LC) evolved as a key technique for chiral separations due to the availability of large number of chiral stationary phases and lesser time to establish a method [30][31][32][33][34][35][36][37][38][39] .…”

Section: Introductionmentioning

confidence: 99%

Development and validation of a chiral LC‐MS method for the enantiomeric resolution of (+) and (−)‐medetomidine in equine plasma by using polysaccharide‐based chiral stationary phases

et al. 2020

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The detection and separation of medetomidine enantiomers from the complex biological matrices poses a great analytical challenge, especially in the field of forensic toxicology and pharmacology. Couple of researchers reported resolution of medetomidine using protein‐based chiral columns, but the reported method is quiet challenging and tedious to be employed for routine analysis. This research paper reported a method that enables the enantio‐separation of medetomidine by using polysaccharide cellulose chiral column. The use of chiralcel OJ‐3R column was found to have the highest potential for successful chiral resolution. Ammonium hydrogen carbonate was the ideal buffer salt for chiral liquid chromatography (LC) with electrospray ionization (ESI)+ mass spectrometry (MS) detection for the successful separation and detection of racemic compound. The method was linear over the range of 0 to 20 ng/mL in equine plasma and the inter‐day precisions of levomedetomidine, dexmedetomidine were 1.36% and 1.89%, respectively. The accuracy of levomedetomidine was in the range of 99.25% to 101.57% and that for dexmedetomidine was 99.17% to 100.99%. The limits of quantification for both isomers were 0.2 ng/mL. Recovery and matrix effect on the analytes were also evaluated. Under the optimized conditions, the validated method can be adapted for the identification and resolution of the medetomidine enantiomers in different matrices used for drug testing and analysis.

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Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-(2-carboxyethylthio)propanoic Acid

Cited by 8 publications

References 1 publication

Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride

Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride

Metabolic Investigation on the Interaction Mechanism between Dietary Dihydrochalcone Intake and Lipid Peroxidation Product Acrolein Reduction

Development and validation of a chiral LC‐MS method for the enantiomeric resolution of (+) and (−)‐medetomidine in equine plasma by using polysaccharide‐based chiral stationary phases

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