Enantioselective pharmacokinetics of mabuterol in rats studied using sequential achiral and chiral HPLC

2005 ◽  
Vol 19 (9) ◽  
pp. 703-708 ◽  
Author(s):  
Xiumei Lu ◽  
Pei Liu ◽  
Huashan Chen ◽  
Feng Qin ◽  
Famei Li
Keyword(s):  
Chiral Hplc ◽  
Enantioselective Pharmacokinetics

Biocatalytic Ketone Reductions Using Biobeads

2020 ◽  
Author(s):  
Jia Shen Chew ◽  
Ken Chi Lik Lee ◽  
THI THANH NHA HO
Keyword(s):  
Enzyme Immobilization ◽  
High Throughput ◽  
High Throughput Screening ◽  
Chiral Hplc ◽  
Micro Scale

<p>Lee and coworkers offers a kind of new concept to enzyme immobilization and explores its suitability in the context of miniaturisation and high-throughput screening. Here, polystyrene-immobilized ketoreductases are compared with its non-immobilized counterparts in terms of conversion and stereoselectivity (both determined by chiral HPLC), and the study indicates that the BioBeads perform similarly (sometimes slightly more selective) which may be useful whenever defined micro-scale amounts of biocatalysts were required in high-throughput experiment settings.</p>

Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers

2006 ◽  
Vol 71 (10) ◽  
pp. 1470-1483 ◽  
Author(s):  
David Šaman ◽  
Pavel Kratina ◽  
Jitka Moravcová ◽  
Martina Wimmerová ◽  
Zdeněk Wimmer
Keyword(s):  
Analytical Data ◽  
Chiral Hplc ◽  
Nmr Analysis ◽  
Target Structure ◽  
Enantiomerically Pure ◽  
Whole Cells ◽  
H Nmr ◽  
Structure Assignment ◽  
Related Compounds ◽  
C Nmr

Glucosylation of the cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexan-1-ol (1a/1b, 2a/2b, 1a or 2a) was performed to prepare the corresponding alkyl β-D-glucopyranosides, mainly to get analytical data of pure enantiomers of the glucosides (3a-6b), required for subsequent investigations of related compounds with biological activity. One of the employed modifications of the Koenigs-Knorr synthesis resulted in achieving 85-95% yields of pure β-anomers 3a/3b, 4a/4b, 3a or 4a of protected intermediates, with several promoters and toluene as solvent, yielding finally the deprotected products 5a/5b, 6a/6b, 5a or 6a as pure β-anomers. To obtain enantiomerically pure β-anomers of the target structure (3a, 4a, 5a and 6a) for unambiguous structure assignment, an enzymic reduction of 2-(4-methoxybenzyl)cyclohexan-1-one by Saccharomyces cerevisiae whole cells was performed to get (1S,2S)- and (1S,2R)-enantiomers (1a and 2a) of 2-(4-methoxybenzyl)cyclohexan-1-ol. The opposite enantiomers of alkyl β-D-glucopyranosides (5b and 6b) were obtained by separation of the diastereoisomeric mixtures 5a/5b and 6a/6b by chiral HPLC. All stereoisomers of the products (3a-6b) were subjected to a detailed 1H NMR and 13C NMR analysis.

scholarly journals Identification of V6.51L as a selectivity hotspot in stereoselective A2B adenosine receptor antagonist recognition

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Xuesong Wang ◽  
Willem Jespers ◽  
Rubén Prieto-Díaz ◽  
Maria Majellaro ◽  
Adriaan P. IJzerman ◽  
...  
Keyword(s):  
Radioligand Binding ◽  
Structural Data ◽  
Binding Mode ◽  
Selective Recognition ◽  
Chiral Hplc ◽  
Binding Assays ◽  
Structural Determinants ◽  
X Ray Crystallography ◽  
Adenosine Receptor Antagonist ◽  
Energy Perturbation

AbstractThe four adenosine receptors (ARs) A1AR, A2AAR, A2BAR, and A3AR are G protein-coupled receptors (GPCRs) for which an exceptional amount of experimental and structural data is available. Still, limited success has been achieved in getting new chemical modulators on the market. As such, there is a clear interest in the design of novel selective chemical entities for this family of receptors. In this work, we investigate the selective recognition of ISAM-140, a recently reported A2BAR reference antagonist. A combination of semipreparative chiral HPLC, circular dichroism and X-ray crystallography was used to separate and unequivocally assign the configuration of each enantiomer. Subsequently affinity evaluation for both A2A and A2B receptors demonstrate the stereospecific and selective recognition of (S)-ISAM140 to the A2BAR. The molecular modeling suggested that the structural determinants of this selectivity profile would be residue V2506.51 in A2BAR, which is a leucine in all other ARs including the closely related A2AAR. This was herein confirmed by radioligand binding assays and rigorous free energy perturbation (FEP) calculations performed on the L249V6.51 mutant A2AAR receptor. Taken together, this study provides further insights in the binding mode of these A2BAR antagonists, paving the way for future ligand optimization.

Optical Resolution of Chiral Buckybowls by Chiral HPLC

2010 ◽  
Vol 39 (6) ◽  
pp. 646-647 ◽  
Author(s):  
Ryoji Tsuruoka ◽  
Shuhei Higashibayashi ◽  
Takeharu Ishikawa ◽  
Shinji Toyota ◽  
Hidehiro Sakurai
Keyword(s):  
Optical Resolution ◽  
Chiral Hplc

ChemInform Abstract: A Convenient Preparation of Optically Active Diepoxyhenicosene (Leucomalure), Lymantrid Sex Pheromone, by Chiral HPLC.

ChemInform ◽  
2010 ◽  
Vol 30 (33) ◽  
pp. no-no
Author(s):  
Masanobu Yamamoto ◽  
Hiroyuki Yamazawa ◽  
Naoto Nakajima ◽  
Tetsu Ando
Keyword(s):  
Sex Pheromone ◽  
Optically Active ◽  
Chiral Hplc ◽  
Convenient Preparation

scholarly journals Neuritogenesis of Herbal (+)- and (−)-Syringaresinols Separated by Chiral HPLC in PC12h and Neuro2a Cells

2002 ◽  
Vol 25 (6) ◽  
pp. 791-793 ◽  
Author(s):  
Kenzo Chiba ◽  
Matsumi Yamazaki ◽  
Emiko Umegaki ◽  
Ming Run Li ◽  
Zhen Wen Xu ◽  
...  
Keyword(s):  
Chiral Hplc ◽  
Neuro2a Cells

Chiral HPLC with carbohydrate carbamates: Influence of support structure on enantioselectivity

Chirality ◽  
1994 ◽  
Vol 6 (2) ◽  
pp. 129-134 ◽  
Author(s):  
Sally J. Grieb ◽  
Stephen A. Matlin ◽  
Joseph G. Phillips ◽  
Ana M. Belenguer ◽  
Harald J. Ritchie
Keyword(s):  
Chiral Hplc ◽  
Support Structure

Solid-phase microextraction and chiral HPLC analysis of ibuprofen in urine

2005 ◽  
Vol 818 (2) ◽  
pp. 285-291 ◽  
Author(s):  
Anderson Rodrigo Moraes de Oliveira ◽  
Evandro José Cesarino ◽  
Pierina Sueli Bonato
Keyword(s):  
Solid Phase Microextraction ◽  
Hplc Analysis ◽  
Solid Phase ◽  
Chiral Hplc

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

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