Enantiomer separation of 2-halomandelic acids via diastereomeric salt formation with chiral N-substituted 2-amino-2-phenylethanols
Chirality. 2023 Nov 13. doi: 10.1002/chir.23630. Online ahead of print.ABSTRACTChiral N-substituted secondary 1,2-aminoalcohols have been developed for the enantioseparation of ortho-halomandelic acids (o-X-MAs) via diastereomeric salt formation. Two structural isomers, N-methyl-2-amino-1,2-diphenylethanol and N-benzyl-2-amino-2-phenylethanol, showed high separation abilities for o-X-MAs (X = Cl, Br, I). The chiral recognition mechanism was elucidated by crystallographic analysis of the less-soluble salts. The substituents on the nitrogen atom of the resolving agents and the inclusion of the crystallization solvent stabili...
Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Koichi Kodama Yumi Kondo Kosei Katayama Moeka Yanagisawa Takuji Hirose Source Type: research
Lipase mediated new chemo-enzymatic synthesis of (RS)-, (R)-, and (S)-bunolol
Chirality. 2023 Nov 13. doi: 10.1002/chir.23627. Online ahead of print.ABSTRACTThe β-adrenergic receptor blocking agents are an important class of drug molecules. The present study reports a new chemo and chemo-enzymatic synthetic process for (RS)-, (R)-, and (S)-bunolol, one of the potent β-adrenergic receptor blocker. In chemo-enzymatic process, CAL L4777 lipase was employed for enantioselective kinetic resolution to synthesize the enantiopure (R)-alcohol and (S)-ester from the corresponding racemic alcohol. Thereafter, the corresponding (R)-alcohol and deacylated (S)-ester were treated with tert-butylamine to produce ...
Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Ravinder Reddy Patlolla Pulivarthi Deepthi Gajjala Raveena Khawlhring Rosangzuala Somarowthu Tejaswini Reddy Shetty Prakasham Linga Banoth Source Type: research
Theoretical study of the interaction between the antibiotic linezolid and the active site of the 50S ribosomal subunit of the bacterium Haloarcula marismortui
Chirality. 2023 Nov 14. doi: 10.1002/chir.23629. Online ahead of print.ABSTRACTFirst antibiotic in the oxazolidinone class, linezolid fights gram-positive multiresistant bacteria by inhibiting protein synthesis through its interaction with the 50S subunit of the functional bacterial ribosome. For its antimicrobial action, it is necessary that its chiral carbon located in the oxazolidinone ring is in the S-conformation. Computational calculation at time-dependent density functional theory methodology, ultraviolet-visible (UV-Vis), and electronic circular dichroism spectra was obtained for noncomplexed and complexed forms of...
Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Giulia Saneti Grandini Nelson Henrique Morgon Aguinaldo Robinson de Souza Source Type: research
Enantiomer separation of 2-halomandelic acids via diastereomeric salt formation with chiral N-substituted 2-amino-2-phenylethanols
Chirality. 2023 Nov 13. doi: 10.1002/chir.23630. Online ahead of print.ABSTRACTChiral N-substituted secondary 1,2-aminoalcohols have been developed for the enantioseparation of ortho-halomandelic acids (o-X-MAs) via diastereomeric salt formation. Two structural isomers, N-methyl-2-amino-1,2-diphenylethanol and N-benzyl-2-amino-2-phenylethanol, showed high separation abilities for o-X-MAs (X = Cl, Br, I). The chiral recognition mechanism was elucidated by crystallographic analysis of the less-soluble salts. The substituents on the nitrogen atom of the resolving agents and the inclusion of the crystallization solvent stabili...
Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Koichi Kodama Yumi Kondo Kosei Katayama Moeka Yanagisawa Takuji Hirose Source Type: research
Lipase mediated new chemo-enzymatic synthesis of (RS)-, (R)-, and (S)-bunolol
Chirality. 2023 Nov 13. doi: 10.1002/chir.23627. Online ahead of print.ABSTRACTThe β-adrenergic receptor blocking agents are an important class of drug molecules. The present study reports a new chemo and chemo-enzymatic synthetic process for (RS)-, (R)-, and (S)-bunolol, one of the potent β-adrenergic receptor blocker. In chemo-enzymatic process, CAL L4777 lipase was employed for enantioselective kinetic resolution to synthesize the enantiopure (R)-alcohol and (S)-ester from the corresponding racemic alcohol. Thereafter, the corresponding (R)-alcohol and deacylated (S)-ester were treated with tert-butylamine to produce ...
Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Ravinder Reddy Patlolla Pulivarthi Deepthi Gajjala Raveena Khawlhring Rosangzuala Somarowthu Tejaswini Reddy Shetty Prakasham Linga Banoth Source Type: research
Theoretical study of the interaction between the antibiotic linezolid and the active site of the 50S ribosomal subunit of the bacterium Haloarcula marismortui
Chirality. 2023 Nov 14. doi: 10.1002/chir.23629. Online ahead of print.ABSTRACTFirst antibiotic in the oxazolidinone class, linezolid fights gram-positive multiresistant bacteria by inhibiting protein synthesis through its interaction with the 50S subunit of the functional bacterial ribosome. For its antimicrobial action, it is necessary that its chiral carbon located in the oxazolidinone ring is in the S-conformation. Computational calculation at time-dependent density functional theory methodology, ultraviolet-visible (UV-Vis), and electronic circular dichroism spectra was obtained for noncomplexed and complexed forms of...
Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Giulia Saneti Grandini Nelson Henrique Morgon Aguinaldo Robinson de Souza Source Type: research
Enantioselective adsorption of ibuprofen enantiomers using chiral-active carbon nanoparticles induced S- α-methylbenzylamine
In this study, we report the preparation of novel chiral carbon nanoparticles (CCNPs) via surface passivation using glucose as the carbon source and S-(-)-α-methylbenzylamine as the chiral ligand. The structures of the obtained CCNPs are characterized via FT-IR, Raman spectroscopy, DLS, XPS, XRD, TEM, and zeta potential analysis. These CCNPs could be employed as the chiral adsorbent and used for the enantioselective adsorption of the ibuprofen enantiomers. The results demonstrated that the CCNPs could selectively adsorb R-enantiomer from ibuprofen racemate solution and give an enantiomeric excess (e.e.) of about 50% under...
Source: Chirality - November 5, 2023 Category: Molecular Biology Authors: Zhenbo Zhao Min Liao Gang Hu Siwen Zeng Li Ge Kedi Yang Source Type: research
Enantioselective adsorption of ibuprofen enantiomers using chiral-active carbon nanoparticles induced S- α-methylbenzylamine
In this study, we report the preparation of novel chiral carbon nanoparticles (CCNPs) via surface passivation using glucose as the carbon source and S-(-)-α-methylbenzylamine as the chiral ligand. The structures of the obtained CCNPs are characterized via FT-IR, Raman spectroscopy, DLS, XPS, XRD, TEM, and zeta potential analysis. These CCNPs could be employed as the chiral adsorbent and used for the enantioselective adsorption of the ibuprofen enantiomers. The results demonstrated that the CCNPs could selectively adsorb R-enantiomer from ibuprofen racemate solution and give an enantiomeric excess (e.e.) of about 50% under...
Source: Chirality - November 5, 2023 Category: Molecular Biology Authors: Zhenbo Zhao Min Liao Gang Hu Siwen Zeng Li Ge Kedi Yang Source Type: research
Enantioselective adsorption of ibuprofen enantiomers using chiral-active carbon nanoparticles induced S- α-methylbenzylamine
In this study, we report the preparation of novel chiral carbon nanoparticles (CCNPs) via surface passivation using glucose as the carbon source and S-(-)-α-methylbenzylamine as the chiral ligand. The structures of the obtained CCNPs are characterized via FT-IR, Raman spectroscopy, DLS, XPS, XRD, TEM, and zeta potential analysis. These CCNPs could be employed as the chiral adsorbent and used for the enantioselective adsorption of the ibuprofen enantiomers. The results demonstrated that the CCNPs could selectively adsorb R-enantiomer from ibuprofen racemate solution and give an enantiomeric excess (e.e.) of about 50% under...
Source: Chirality - November 5, 2023 Category: Molecular Biology Authors: Zhenbo Zhao Min Liao Gang Hu Siwen Zeng Li Ge Kedi Yang Source Type: research
Enantioselective adsorption of ibuprofen enantiomers using chiral-active carbon nanoparticles induced S- α-methylbenzylamine
In this study, we report the preparation of novel chiral carbon nanoparticles (CCNPs) via surface passivation using glucose as the carbon source and S-(-)-α-methylbenzylamine as the chiral ligand. The structures of the obtained CCNPs are characterized via FT-IR, Raman spectroscopy, DLS, XPS, XRD, TEM, and zeta potential analysis. These CCNPs could be employed as the chiral adsorbent and used for the enantioselective adsorption of the ibuprofen enantiomers. The results demonstrated that the CCNPs could selectively adsorb R-enantiomer from ibuprofen racemate solution and give an enantiomeric excess (e.e.) of about 50% under...
Source: Chirality - November 5, 2023 Category: Molecular Biology Authors: Zhenbo Zhao Min Liao Gang Hu Siwen Zeng Li Ge Kedi Yang Source Type: research
Enantioselective adsorption of ibuprofen enantiomers using chiral-active carbon nanoparticles induced S- α-methylbenzylamine
In this study, we report the preparation of novel chiral carbon nanoparticles (CCNPs) via surface passivation using glucose as the carbon source and S-(-)-α-methylbenzylamine as the chiral ligand. The structures of the obtained CCNPs are characterized via FT-IR, Raman spectroscopy, DLS, XPS, XRD, TEM, and zeta potential analysis. These CCNPs could be employed as the chiral adsorbent and used for the enantioselective adsorption of the ibuprofen enantiomers. The results demonstrated that the CCNPs could selectively adsorb R-enantiomer from ibuprofen racemate solution and give an enantiomeric excess (e.e.) of about 50% under...
Source: Chirality - November 5, 2023 Category: Molecular Biology Authors: Zhenbo Zhao Min Liao Gang Hu Siwen Zeng Li Ge Kedi Yang Source Type: research
Enantioselective adsorption of ibuprofen enantiomers using chiral-active carbon nanoparticles induced S- α-methylbenzylamine
In this study, we report the preparation of novel chiral carbon nanoparticles (CCNPs) via surface passivation using glucose as the carbon source and S-(-)-α-methylbenzylamine as the chiral ligand. The structures of the obtained CCNPs are characterized via FT-IR, Raman spectroscopy, DLS, XPS, XRD, TEM, and zeta potential analysis. These CCNPs could be employed as the chiral adsorbent and used for the enantioselective adsorption of the ibuprofen enantiomers. The results demonstrated that the CCNPs could selectively adsorb R-enantiomer from ibuprofen racemate solution and give an enantiomeric excess (e.e.) of about 50% under...
Source: Chirality - November 5, 2023 Category: Molecular Biology Authors: Zhenbo Zhao Min Liao Gang Hu Siwen Zeng Li Ge Kedi Yang Source Type: research
Investigation into the performance and stability of immobilized and coated polysaccharide columns in supercritical fluid chromatography
In this study, the performance of the widely used "golden four" coated chiral stationary phases (Chiralpak AD-3, Chiralcel OD-3, Chiralpak AS-3, and Chiralcel OJ-3) was compared with their corresponding immobilized versions (Chiralpak IA-3, Chiralpak IB-3, Chiralpak IB N-3, Chiralpak IH-3, and Chiralpak IJ-3) under supercritical fluid chromatography (SFC) conditions with a set of 30 racemic compounds. Using the traditional modifiers, methanol and isopropanol, the immobilized columns (Chiralpak IB N-3 and Chiralpak IH-3) showed an improved general ability to successfully resolve the enantiomers of the target analytes relati...
Source: Chirality - November 3, 2023 Category: Molecular Biology Authors: Lei Yue Madeline Yeh John Reilly Bing Wang Christopher J Welch Maria Phan Source Type: research
Investigation into the performance and stability of immobilized and coated polysaccharide columns in supercritical fluid chromatography
In this study, the performance of the widely used "golden four" coated chiral stationary phases (Chiralpak AD-3, Chiralcel OD-3, Chiralpak AS-3, and Chiralcel OJ-3) was compared with their corresponding immobilized versions (Chiralpak IA-3, Chiralpak IB-3, Chiralpak IB N-3, Chiralpak IH-3, and Chiralpak IJ-3) under supercritical fluid chromatography (SFC) conditions with a set of 30 racemic compounds. Using the traditional modifiers, methanol and isopropanol, the immobilized columns (Chiralpak IB N-3 and Chiralpak IH-3) showed an improved general ability to successfully resolve the enantiomers of the target analytes relati...
Source: Chirality - November 3, 2023 Category: Molecular Biology Authors: Lei Yue Madeline Yeh John Reilly Bing Wang Christopher J Welch Maria Phan Source Type: research
Investigation into the performance and stability of immobilized and coated polysaccharide columns in supercritical fluid chromatography
In this study, the performance of the widely used "golden four" coated chiral stationary phases (Chiralpak AD-3, Chiralcel OD-3, Chiralpak AS-3, and Chiralcel OJ-3) was compared with their corresponding immobilized versions (Chiralpak IA-3, Chiralpak IB-3, Chiralpak IB N-3, Chiralpak IH-3, and Chiralpak IJ-3) under supercritical fluid chromatography (SFC) conditions with a set of 30 racemic compounds. Using the traditional modifiers, methanol and isopropanol, the immobilized columns (Chiralpak IB N-3 and Chiralpak IH-3) showed an improved general ability to successfully resolve the enantiomers of the target analytes relati...
Source: Chirality - November 3, 2023 Category: Molecular Biology Authors: Lei Yue Madeline Yeh John Reilly Bing Wang Christopher J Welch Maria Phan Source Type: research
