Abstract:
:We report a method to determine the absolute configuration of alpha-amino acids by exciton coupled circular dichroism (ECCD). Naturally occurring amino acids were successfully derivatized with 2-bromomethylquinoline. Complexation of these conformationally flexible ligands with Cu(II) salts yielded defined propeller-like structures. The direction of the twist (i.e., the relative orientation of the chromophores to each other) is governed by the asymmetric amino acid carbon center. The transition moments of the chromophores couple and yield a bisignate circular dichroism spectrum, the sign of which corresponds to the absolute configuration of the chiral center of the amino acid. Enantiomeric excess (e.e.) of amino acid derivatives is linearly related to the differential extinction coefficient Delta(epsilon) and can be assessed easily utilizing a standard curve. This efficient, sensitive technique requires low analyte concentrations, offers several advantages over established methods, and could be applied in medicinal, pharmaceutical, or chemical retail and manufacturing industry.
journal_name
Chiralityjournal_title
Chiralityauthors
Holmes AE,Zahn S,Canary JWdoi
10.1002/chir.10079subject
Has Abstractpub_date
2002-06-01 00:00:00pages
471-7issue
6eissn
0899-0042issn
1520-636Xjournal_volume
14pub_type
杂志文章相关文献
CHIRALITY文献大全abstract::Bath salts, fumigations, cleaners and air fresheners, behind these terms substances are hidden, which count as "Legal Highs". These fancy names are used to pretend Legal Highs as harmless compounds, to circumvent legal regulations for marketing as well as to increase the sales. Besides classic illicit drugs of synthet...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23135
更新日期:2020-01-01 00:00:00
abstract::A statement has been formulated that chirality is an indispensable inherent property of all material objects, at one level of organization of matter or another. The translation of chirality from one level of material objects to another deserves our attention. The parity violation of weak interactions can be discussed ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20271
更新日期:2006-08-01 00:00:00
abstract::Three aldohexoses, glucose, galactose, and mannose, and three aldopentoses, arabinose, xylose, and ribose, were derivatized with L-tryptophanamide (L-TrpNH2 ) under alkaline conditions. Using a basic mobile phase (pH 9.2), the three aldohexoses or the three aldopentoses were simultaneously enantioseparated, respective...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22456
更新日期:2015-07-01 00:00:00
abstract::We present a new concept of synthesis for preparation of molecularly imprinted polymers using a functionalized initiator to replace the traditional functional monomer. Using propranolol as a model template, a carboxyl-functionalized radical initiator was demonstrated to lead to high-selectivity polymer particles prepa...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23167
更新日期:2020-03-01 00:00:00
abstract::Supercritical fluid chromatography (SFC) is already used for enantioseparation in the pharmaceutical industry, but it is rarely used for the separation of chiral pesticides. Comparing with high performence liquid chromatography, SFC uses much more environmnetal friendly and economic mobile phase, supercritical CO2 . I...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22836
更新日期:2018-05-01 00:00:00
abstract::The size, sign, and profile of induced circular dichroism (CD) features in the Soret region are reliable indicators of the binding modes of porphyrins and metalloporphyrins to DNA. Porphyrins shown (using such CD criteria) to be intercalators in monodispersed DNA duplexes prove extremely useful for the detection and c...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.10206
更新日期:2003-05-05 00:00:00
abstract::Cyclodextrins that are indiscriminately carboxymethylated at the 2-, 3-, and 6-positions are used as chiral NMR solvating agents for cationic substrates with phenyl, naphthyl, pyridyl, indoline, and indole rings. Enantiodifferentiation with the alpha-, beta-, and gamma-cyclodextrin derivatives is compared. The carboxy...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20748
更新日期:2010-03-01 00:00:00
abstract::Fourier transform infrared vibrational circular dichroism (FTIR-VCD) measurements have gone through major advances in the last decade. A major thrust in these advances was to find ways that can minimize the VCD spectral artifacts and obtain the VCD signals at enhanced signal quality. However, all these advances are no...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20999
更新日期:2011-10-01 00:00:00
abstract::[3β,5β,7α,12α]-3-(4-t-Butylbenzoilamine)-7,12-dihydroxycholan-24-oic acid was synthesized and recrystallized from chlorobenzene and acetone. Orthorhombic P2(1)2(1)2(1) and monoclinic P2(1) crystals were obtained, respectively, and both crystals include solvent and water molecules with a 1:1:1 stoichiometry. In the sec...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.21020
更新日期:2011-11-01 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
abstract::One of the most powerful techniques that are currently available to measure thermodynamic parameters such as enthalpy (ΔH), Gibbs free energy (ΔG), entropy changes (ΔS), and binding affinity in chemical reactions is isothermal titration calorimetry (ITC). Recent advances in instrumentation have facilitated the develop...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.22842
更新日期:2018-05-01 00:00:00
abstract::An increase in both retention and enantioselectivity for some beta-blocking agents was observed when exchanging potassium to sodium ion in the buffer used as mobile phase. A large effect of ionic strength on retention was observed, while the enantioselectivity was constant. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:6<513::AID-CHIR2>3
更新日期:1998-01-01 00:00:00
abstract::Kynurenic acid (KYNA), an endogenous antagonist of N-methyl-D-aspartate and α(7) nicotinic acetylcholine receptors, is one of the L-tryptophan (Trp) metabolites. To compare the level of KYNA produced in the striatum of rats after independent administration of L-Trp and D-Trp, rats were intraperitoneally administered L...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20938
更新日期:2011-01-01 00:00:00
abstract::An environmental and sensitive sample pretreatment method was established and combined with high-performance liquid chromatography (HPLC) for the analysis of tetracycline hydrochloride (TC) in feed water and lake water. One element small molecule alcohol-salt aqueous two-phase system (ATPS) cannot effectively adjust t...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23080
更新日期:2019-09-01 00:00:00
abstract::Glutathione (GSH) conjugation of the chiral compound 2-bromo-3-phenylpropionic acid (BPP) was studied in vitro and in the rat in vivo. GSH conjugation of BPP, catalyzed by a mixture of glutathione-S-transferases (GST's) from rat liver cytosol in vitro, was stereoselective: at a substrate concentration of 250 microM, (...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530040702
更新日期:1992-01-01 00:00:00
abstract::A simple one-dimensional (13)C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of α-tocopherol. To achieve this the chiral solvating agent (S)-(+)-1-(9-anthryl)-2,...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22535
更新日期:2015-11-01 00:00:00
abstract::Experimental studies suggest that amide bond may significantly deviate from planar arrangement even in linear peptides and proteins. In order to find out the extent to which such deviation may influence principal amide spectroscopic properties, we conducted a computational study of nonplanar N-methylacetamide (NMA) co...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20462
更新日期:2007-11-01 00:00:00
abstract::Parallel kinetic resolution of Evans' phenylglycine derived oxazolidinone using an equimolar combination of quasi-enantiomeric active esters (derived from [D,13C]-labeled 2-phenylpropionic acid) was achieved. The levels of stereocontrol were high, leading to products with predictable configurations. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20367
更新日期:2007-05-05 00:00:00
abstract::A sensitive and stereospecific liquid chromatography-tandem mass spectrometry method for the quantitative determination of TWo8 enantiomers ((2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol) was developed and validated in rat serum and some tissues. Racemic TWo8 is a new chemical ent...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22011
更新日期:2012-08-01 00:00:00
abstract::After alkylation of a fraction of the total alpha-adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (-)- and (+)-epinephrine in functional studies were 7 X 10(-7) M and 2 X 10(-5) M, respectively. In the adrenoreceptor-containing tissue fraction, when 3H-labeled WB4101 was used as ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530010106
更新日期:1989-01-01 00:00:00
abstract::Ion channels are pharmacologic receptors and as such exhibit stereoselective interactions with drugs. Ion channels are conformationally mobile transmembrane proteins existing in a number of open and closed states. Drug interactions with these different states may differ quantitatively and qualitatively. Stereoselectiv...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/(SICI)1520-636X(1996)8:1<35::AID-CHIR8>3.0
更新日期:1996-01-01 00:00:00
abstract::Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient wa...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20663
更新日期:2009-07-01 00:00:00
abstract::A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the al...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;
更新日期:2000-08-01 00:00:00
abstract::The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalid...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20398
更新日期:2007-06-01 00:00:00
abstract::We demonstrate by using vibrational circular dichroism (VCD) spectroscopy that it is possible to investigate the chirality of a supramolecular polymeric system in relatively dilute solutions. Chiral C(3)-symmetrical discotic molecules, based on a trialkylbenzene-1,3,5-carboxamide, form supramolecular columnar stacks w...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20568
更新日期:2008-09-01 00:00:00
abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10287
更新日期:2003-11-01 00:00:00
abstract::Racemic N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5), a putative postsynaptic agonist and presynaptic antagonist at muscarinic receptors, was resolved into the enantiomers by a new method suitable for large scale preparation. The method involves a chemoselective N-debenzylation as the key step. The en...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530040607
更新日期:1992-01-01 00:00:00
abstract::Vibrational circular dichroism (VCD) spectra of (+)-alpha-pinene solutions in carbon tetrachloride have been measured in the range of volume fractions 5-100% (v/v) in the mid-infrared region. The concentration dependence measured was statistically analyzed with the aim of obtaining a reliable correlation between the V...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3
更新日期:2000-05-01 00:00:00
abstract::The biodegradation of the chiral phenoxyalkanoic herbicides 2-(2,4-dichlorophenoxy)propionic aid (2,4-DP) and 2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) was investigated using enantioselective HPLC and chiroptical detection. Racemic mixtures of 2,4-DP and MCPP were applied to three species of turf grass, four s...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1999)11:4<330::AID-CHIR12>
更新日期:1999-01-01 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