Abstract:
:Four racemic esters of (1R*,7aR*)-3,6,7,7a-tetrahydro-1-hydroxy-7a-methyl-1H-inden-5(2H)-one were prepared and subjected to hydrolysis with two types of hydrolases, including alcalase and three lipases. Alcalase and lipase showed opposite enantiopreference on these esters. Based on this result, we developed a gram-scale procedure using butanoate as the substrate, which was treated consecutively with alcalase and lipase from Candida rugosa (CRL), to give both enantiomers of the title compound in high yields and high enantiomeric excess.
journal_name
Chiralityjournal_title
Chiralityauthors
Lo LC,Chou TC,Shie JJdoi
10.1002/chir.20023subject
Has Abstractpub_date
2004-05-05 00:00:00pages
267-71issue
4eissn
0899-0042issn
1520-636Xjournal_volume
16pub_type
杂志文章相关文献
CHIRALITY文献大全abstract::The objective of this brief highlight is to point out the central role of the exciton chirality method to gain insights on the structural basis of the recently achieved ligand gating of synthetic ion channels. This unprecedented ligand gating was achieved with an equally unprecedented transmembrane rigid-rod pi-stack ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20221
更新日期:2006-02-01 00:00:00
abstract::Benalaxyl (BX), methyl-N-phenylacetyl-N-2,6-xylyl alaninate, is a potent acylanilide fungicide and consist of a pair of enantiomers. The stereoselective metabolism of BX was investigated in rat and rabbit microsomes in vitro. The degradation kinetics and the enantiomer fraction (EF) were determined using normal high-p...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20879
更新日期:2011-02-01 00:00:00
abstract::Searching the 3D structural fragments of organic molecules is challenging because of structural differences between X-ray and theoretically calculated geometries and the conformational flexibility of substituents. The codification program called Conformational Code for Organic Molecules (CCOM) can be used to unambiguo...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22596
更新日期:2016-05-01 00:00:00
abstract::An optically active spiropyran 1 with a binaphthol moiety as a chiral source was synthesized. The colored merocyanine form of (R)-1 obtained by the UV irradiation remained in the presence of D-amino acids longer than with L-amino acids. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10111
更新日期:2002-10-01 00:00:00
abstract::Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dica...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20377
更新日期:2007-03-01 00:00:00
abstract::Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush borde...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:4<349::AID-CHIR10>
更新日期:1998-01-01 00:00:00
abstract::The stereochemistry of tolperisone, a chiral aryl-alkyl basic ketone was investigated by means of circular dichroism (CD) and ultraviolet (UV) spectroscopy. The unusually high optical activity of tolperisone hydrochloride in the n-->pi* region is interpreted by the presence of a chiral conformer in solution. For stere...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/1520-636X(2000)12:10<720::AID-CHIR4>3.0.CO
更新日期:2000-11-01 00:00:00
abstract::The resolution methods applying (-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ("TADDOL"), (-)-(2R,3R)-α,α,α',α'-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol ("spiro-TADDOL"), as well as the acidic and neutral Ca(2+) salts of (-)-O,O'-dibenzoyl- and (-)-O,O'-di-p-toluoyl-(2R,3R)-tartaric acid ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22293
更新日期:2014-03-01 00:00:00
abstract::Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkene...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20689
更新日期:2010-07-01 00:00:00
abstract::Copper(II) complexes of N2-octyl-(S)-phenylalaninamide (Noc-Phe-NH2), N2-dodecyl-(S)-phenylalaninamide (Ndo-Phe-NH2), and N2-octyl-(S)-norleucinamide (Noc-NLeu-NH2), dynamically adsorbed on a reversed-phase C18 column, were able to perform the direct enantiomeric separation of unmodified amino acids, amino acid amides...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1996)8:2<189::AID-CHIR3>3.
更新日期:1996-01-01 00:00:00
abstract::In order to cope with the increasing number of publications on the separation of enantiomers by chromatography on a chiral stationary phase, the graphical molecular database CHIRBASE was created. In the present state, the database package covers information (structural, bibliographic, and chromatographic data) on liqu...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530050404
更新日期:1993-01-01 00:00:00
abstract::rac-Isradipine is a dihydropyridine type calcium antagonist. Its calcium entry blocking effect is due primarily to the (+)-(S)-enantiomer. This study describes a sensitive enantioselective method for the determination of isradipine in human serum. Following alkaline extraction into hexane, the enantiomers of isradipin...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:9<808::AID-CHIR6>3
更新日期:1998-01-01 00:00:00
abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:5/6<464::AID-CHIR2
更新日期:2000-06-01 00:00:00
abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22008
更新日期:2012-09-01 00:00:00
abstract::Kinetic and equilibrium binding studies were performed on the interaction of warfarin enantiomers with human serum albumin (HSA) in the absence and presence of lorazepam acetate (LoAc) enantiomers. Binding kinetics were followed by recording changes in the fluorescence of warfarin upon binding to HSA using the stopped...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10113
更新日期:2002-05-15 00:00:00
abstract::The epimeric diterpenes (+)-(1S,3E,7E,11S,12S)-verticilla-3,7-dien-12-ol (1), isolated from Bursera suntui, and (+)-(1S,3E,7E,11S,12R)-verticilla-3,7-dien-12-ol (2), isolated from Bursera kerberi, gave the same Wagner-Meerwein rearrangement product (-)-(1E,4Z,8Z,11S,12R)-phomacta-1,(15)4,8-triene (3). The Et2 O:BF3 -i...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23061
更新日期:2019-11-01 00:00:00
abstract::Despite the fact that several studies have reported the concentrations of various free amino acids in tobacco, their enantiomeric composition is unknown. Both the absolute and enantiomeric compositions of proline, alanine, asparagine, aspartic acid, valine, methionine, leucine,and phenylalanine were determined for thr...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1999)11:8<669::AID-CHIR10>
更新日期:1999-01-01 00:00:00
abstract::Metoprolol is available for clinical use as a racemic mixture. The S-(-)-metoprolol enantiomer is the one expressing higher activity in the blockade of the β(1)-adrenergic receptor. The α-hydroxymetoprolol metabolite also has activity in the blockade of the β(1)-adrenergic receptor. The present study describes the dev...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22102
更新日期:2013-01-01 00:00:00
abstract::The hemicryptophane racemate (±)-1 was optically resolved by semipreparative HPLC on Chiralpak IC column. The absolute configuration of each isolated enantiomer was established from the analysis of their electronic circular dichroism spectra. Enantiodifferentiation of the chiral cationic cage (±)-1 was evidenced in so...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22100
更新日期:2012-12-01 00:00:00
abstract::The special relationship between France and the polarization of light from the beginning of the 19th century until the present day is reviewed in the lives and works of Étienne Louis Malus, François Arago, Jean-Baptiste Biot, Augustin Fresnel, Louis Pasteur, Frédéric Wallerant, Aimé Cotton, Francis Perrin, and Alain A...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22818
更新日期:2018-04-01 00:00:00
abstract::C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.1053
更新日期:2001-08-01 00:00:00
abstract::This review brings together the past and current methods for synthesizing the classical cucurbit[n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as " classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methy...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.22363
更新日期:2014-11-01 00:00:00
abstract::The hydrolysis and acyl migration of biosynthetic S-naproxen-beta-l-O-acyl glucuronide (I) and R-naproxen-beta-l-O-acyl glucuronide (II) was followed by HPLC. Nine first-order kinetic rate constants for the hydrolysis and acyl migration between the beta-l-O-acyl glucuronide, its alpha/beta-2, alpha/beta-3-, alpha/beta...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10047
更新日期:2002-05-05 00:00:00
abstract::Both epimers of the naturally occurring nonproteinogenic amino acid L-cyclopentenylglycine, (2S,1'S)- and (2S, 1'R)-2-(cyclopent-2'-enyl)glycine, were obtained via a procedure involving condensation of 3-chlorocyclopentene with diethyl acetylaminomalonate, deethoxycarbonylation, chromatographic separation of the resul...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;
更新日期:2000-10-01 00:00:00
abstract::A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K2 CO3 (10 mol%) with high efficiency in water/ethanol as gr...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22653
更新日期:2016-11-01 00:00:00
abstract::The separation methods of the enantiomers of two β-blockers and tryptophan were studied using capillary electrochromatography with heparin covalently as well as non-covalently, bonded onto the capillary inner wall as stationary phase and electrokinetic chromatography with heparin as pseudostationary phase. In the case...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22972
更新日期:2018-06-25 00:00:00
abstract::The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comp...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23131
更新日期:2019-11-01 00:00:00
abstract::Four Ala-Ala dipeptides with a perfluoroalkyl chain at the N-terminal were synthesized. They were able to self-assemble into helical nanofibers and/or twisted nanobelts in a mixture of DMSO/H2 O. The handedness of nanofibers and nanobelts was controlled by the chirality of the alanine at the N-terminal. The stacking h...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23130
更新日期:2019-11-01 00:00:00
abstract::Two "click" binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatography. Their structures incorporate S-(-)-1,1'-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of rac...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22039
更新日期:2012-05-01 00:00:00
abstract::Experimental hyperlipidemia has shown to decrease cytochrome P450 3A4 and 2C11 expression and to increase liver concentrations and the plasma protein binding of halofantrine (HF) enantiomers. The present study examined the effect of hyperlipidemic (HL) serum on the metabolism of HF enantiomers by primary rat hepatocyt...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22054
更新日期:2012-07-01 00:00:00