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 resulting two pairs of enantiomers, and enzymatic resolution of the racemates employing enantioselective hydrolysis of the ethyl ester group with alpha-chymotrypsin. The method was used for preparation of (13)C-labeled compounds of interest for biosynthetic tracer experiments. Enantiomeric purity of the products was determined by chiral HPLC on a Crownpak CR(+) column. The biologically active (2S,1'R) isomer was obtained as a pure compound and characterized for the first time. The (2R,1'R) and (2R,1'S) isomers were obtained as N-acetyl ethyl ester derivatives.
journal_name
Chiralityjournal_title
Chiralityauthors
Andersen L,Nielsen B,Jaroszewski JWdoi
10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;subject
Has Abstractpub_date
2000-10-01 00:00:00pages
665-9issue
9eissn
0899-0042issn
1520-636Xpii
10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;journal_volume
12pub_type
杂志文章相关文献
CHIRALITY文献大全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::Rabeprazole is an effective proton pump inhibitor to treat acid-related diseases. To achieve the simultaneous determination of rabeprazole enantiomers in human plasma, a chiral LC-MS/MS method was developed and validated. Acetonitrile including 0.1% ammonium were used as protein precipitating agent. Analytes were sepa...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23022
更新日期:2018-12-01 00:00:00
abstract::1alpha,25-Dihydroxyvitamin D(3) (1alpha,25(OH)2D3) has been shown to modulate not only proliferation and differentiation, but also apoptosis in malignant cells, indicating that it could be useful for the treatment of cancer and psoriasis. However, little information has been available on the binding conformation of th...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.1046
更新日期:2001-07-01 00:00:00
abstract::Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0
更新日期:2000-01-01 00:00:00
abstract::The chiral squaramide catalysts (8-15) were synthesized, and their catalytic efficiency in the enantioselective conjugate addition of pyrazolones to nitroalkenes was described. This protocol provides excellent chemical yields (up to 93%) of chiral 5-methyl-4-(2-nitro-1-arylethyl)pyrazol-3-ol derivatives with high enan...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23295
更新日期:2021-01-11 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::Spontaneous symmetry breaking in reactive systems, known as a rare physical phenomenon and for the Soai autocatalytic irreversible reaction, might in principle also occur in other, more common asymmetric reactions when the chiral product is capable to promote its formation and an element of "nonlinearity" is involved ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20474
更新日期:2007-11-01 00:00:00
abstract::This study focused on the chiral characteristics of methamphetamine seizures in Shanghai for inferring the synthetic pathways of drugs. Capillary electrophoresis coupled to time-of-flight mass spectrometry was used for simultaneous chiral separation of amphetamine-type stimulants and ephedrine, including S(+)-amphetam...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22987
更新日期:2018-09-01 00:00:00
abstract::Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak I...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22690
更新日期:2017-03-01 00:00:00
abstract::The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl-1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mob...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20944
更新日期:2011-01-01 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::Vitamin E is an essential nutrient of still increasing economic importance. Vitamin E derivatives include many nonracemic chiral compounds whose chirooptical characterization is scarcely described in the literature. We report the CD spectra of delta-tocopherol and its unsaturated analog delta-tocotrienol. TDDFT calcul...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20591
更新日期:2009-01-01 00:00:00
abstract::A comparison of the enantiomeric resolution of (+/-)-threo-methylphenidate (MPH) (Ritalin) was achieved on different polysaccharide based chiral stationary phases. The mobile phase used was hexane-ethanol-methanol-trifluoroacetic acid (480:9.75:9.75:0.5, v/v/v/v). Benzoic acid and phenol were used as the mobile phase ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10028
更新日期:2002-01-01 00:00:00
abstract::The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. B...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20396
更新日期:2007-06-01 00:00:00
abstract::(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro-acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild con...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20728
更新日期:2010-02-01 00:00:00
abstract::Vibrational circular dichroism spectra (VCD) in the mid-IR region and electronic circular dichroism (ECD) spectra for three carnitine derivatives in the form of hydrochloride salts were recorded in deuterated methanol solutions. Density Functional Theory calculations help one to understand the significance of the obse...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22532
更新日期:2015-12-01 00:00:00
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-sca...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20023
更新日期:2004-05-05 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::Nine patients taking oral doses of 10 mg/12 h rac-pindolol as part of their treatment for hypertension in pregnancy were recruited for the study. Maternal and fetal gestational age ranged from 20-38 years and 28-41 weeks, respectively. Blood was collected from the umbilical cord vein and from the mother from zero to 1...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10124
更新日期:2002-08-01 00:00:00
abstract::E-6087 is a nonsteroidal anti-inflammatory compound that selectively inhibits cyclooxygenase-2. Because E-6087 has a chiral center, this compound is a racemic mixture of two stereoisomers, (+)-(R)-E-6087 (E-6231) and (-)-(S)-E-6087 (E-6232). A normal-phase liquid-chromatographic method for the enantioselective determi...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20030
更新日期:2004-05-15 00:00:00
abstract::The assignment of the absolute configuration of novel anti-inflammatory pyrrole derivatives has been accomplished by a combined strategy based on independent physical methods. The key step of our stereochemical characterization approach is the production at mg-scale of enantiomerically pure forms by HPLC on Chiralpak ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20518
更新日期:2008-06-01 00:00:00
abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...
journal_title:Chirality
pub_type: 临床试验,杂志文章
doi:10.1002/(SICI)1520-636X(1999)11:1<29::AID-CHIR5>3.
更新日期:1999-01-01 00:00:00
abstract::Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal ami...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22861
更新日期:2018-06-01 00:00:00
abstract::A series of 1,4-disubstituted piperazine derivatives with hypnotic activity were examined on three polysaccharide-based chiral stationary phases, namely, Chiracel OD, Chiracel OJ and Chiralpak AD. It was possible to resolve all the compounds on all the phases examined (1.13 = alpha = 3.54). Cellulose tris(4-methyl...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1999)11:10<790::AID-CHIR9>
更新日期:1999-01-01 00:00:00
abstract::Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-perf...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23206
更新日期:2020-05-01 00:00:00
abstract::The macrocyclic glycopeptide, ristocetin A, was covalently bonded to a silica gel support and evaluated as a liquid chromatographic (LC) chiral stationary phase (CSP). Over 230 racemates were resolved in either the reversed-phase mode, the normal-phase mode, or the polar-organic mode. The retention behavior and select...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:5<434::AID-CHIR10>
更新日期:1998-01-01 00:00:00
abstract::The chiral fungicide furametpyr is widely used in the rice field to control rice sheath blight; however, furametpyr enantiomers are treated as just one compound in traditional achiral analysis, which gives only partial information. An effective chiral analytical method was developed for the resolution and determinatio...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22232
更新日期:2013-12-01 00:00:00
abstract::(S)-(-)-2-(α-hydroxyethyl)-benzimidazole and (S)-(+)-2-(α-hydroxybenzyl)-benzimidazole work as chiral Brønsted bases (BBs) in Diels-Alder reaction between anthrone and maleimides under mild reaction condition. These chiral BBs cause asymmetric induction. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20942
更新日期:2011-05-01 00:00:00
abstract::Chiral pesticides are now receiving more and more attention in the food-making process. This experiment studied the enantioselective behavior of diclofop-methyl (DM) and its main metabolite, diclofop (DC), during the soy sauce brewing process. Two kinds of commonly used strains, Aspergillus oryzae and Saccharomyces ro...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22545
更新日期:2016-01-01 00:00:00
abstract::One- and two-color, mass selected R2PI spectra of the S(1)<--S(0) transitions in the bare (+)-(R)-1-phenyl-1-ethanol (E(R)) and its complexes with different solvent molecules (solv) (-)-(R)-2-butanol (B(R)) or (+)-(S)-2-butanol (B(S)) and (-)-(R)-2-butylamine (A(R)) or (+)-(S)-2-butylamine (A(S)), have been recorded a...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10010
更新日期:2001-01-01 00:00:00