Requirements in structure for chiral recognition of chitosan derivatives.

In order to investigate the influence of a minor variation in structure of N-acyl chitosan derivatives on enantioseparation, chiral selectors (CSs) of chitosan 3,6-bis(phenylcarbamate)-2-(phenylacetamide)s and chitosan 3,6-bis(phenylcarbamate)-2-(cyclohexylacetamide)s were synthesized. The corresponding chiral stationary phases (N-PhAc CSPs and N-cHeAc CSPs) were also prepared, respectively, with the two series of CSs. Enantioseparation results revealed that the N-PhAc CSPs were better than the N-cHeAc ones in enantioseparation.

Conversion of azidoamylose to ureidoamylose carbamates in one-pot reactions.

In order to covert azidoamylose into ureidoamylose derivatives in a facile way, 6-azido-6-deoxyamylose was reacted with triphenylphosphine, and then with water and a phenyl isocyanate in turn. The obtained product was amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea), which was synthesized through three reactions in a one-pot method. The essential point to ensure the method be successful was that the water should be fed at an appropriate amount.

Chiral separation materials based on derivatives of 6-amino-6-deoxyamylose.

In order to develop new type of chiral separation materials, in this study, 6-amino-6-deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6-amino-6-deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high-performance liquid chromatography. The resulted 6-amido-6-deoxyamyloses and amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s were characterized by IR, H NMR, and elemental analysis.

The interactions between chiral analytes and chitosan-based chiral stationary phases during enantioseparation.

The goal of the present study was to disclose the interactions between chitosan-type chiral selectors (CSs) and chiral analytes during enantioseparation. Hence, six chitosan 3,6-bis(phenylcarbamate)-2-(cyclohexylmethylurea)s were synthesized and characterized. These chitosan derivatives were employed as CSs with which the corresponding coated-type chiral stationary phases (CSPs) were prepared.

Probing Activity Enhancement of Photothermal Catalyst under Near-Infrared Irradiation.

Exploring highly efficient catalysts with excellent photothermal conversion and further unveiling their catalytic mechanism are of significant importance for photothermal catalysis technologies, but there remain grand challenges to these activities. Herein, we fabricate a nest-like photothermal nanocatalyst with Pd decorated on a N-doped carbon functionalized BiS nanosphere (BiS@NC@Pd). Given its well-dispersed ultrafine Pd nanoparticles and the excellent photothermal heating ability of support material, the BiS@NC@Pd composite exhibits a superior activity and photothermal conversion property to commercial Pd/C catalyst for hydrogenation of organic dyes upon exposure to near-infrared (NIR) light irradiation.

Comparison in enantioseparation performance of chiral stationary phases prepared from chitosans of different sources and molecular weights.

The aim of the present study was to compare the enantioseparation performance of chiral stationary phases (CSPs) which were derived from chitosans of different sources and molecular weights. Therefore, chitosans of shrimp and crab shells were prepared. The viscosity-average molecular weights of the chitosans both prepared from shrimp and crab shells were 2.

Structure screening and performance restoration of chiral separation materials based on chitosan derivatives.

In order to screen chiral selector structure and find structure-property relationship, ten chitosan 3,6-bis(phenylcarbamate)-2-(cyclopropylformamide)s were synthesized from which corresponding chiral stationary phases were prepared. Enantioseparation capability and mobile phase tolerability of the chiral stationary phases were evaluated. The chiral selectors with 3-chloro-4-methylphenyl, 4-chlorophenyl, 3-chlorophenyl, 3,5-dichlorophenyl and 4-trifluoromethoxyphenyl groups demonstrated powerful enantioseparation capability.

Performances comparison of enantiomeric separation materials prepared from shrimp and crab shells.

Previously reported studies demonstrate that many chitin/chitosan derivatives are promising for enantioseparation of chiral compounds. The aim of the present study is to investigate influence of the chitin sources on performances of the chitosan type enantiomeric separation materials. Therefore, the chitosans were prepared from crab and shrimp shells, from which two sets of chiral selector, i.

Incidence of second-time lateral patellar dislocation is associated with anatomic factors, age and injury patterns of medial patellofemoral ligament in first-time lateral patellar dislocation: a prospective magnetic resonance imaging study with 5-year follow-up.

Purpose: To examine the predictors of the second-time lateral patellar dislocation (LPD) in patients after acute first-time LPD in a 5-year follow-up.

Methods: Data were collected prospectively from patients after acute first-time LPD with conservative treatment. Factors included sex, age at the first-time LPD, anatomical variants [trochlear dysplasia, patellar height, tibial tuberosity-trochlear groove (TT-TG) distance], and injury patterns of medial patellofemoral ligament (MPFL) in acute first-time LPD.

A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation.

N-Methoxycarbonyl chitosan was prepared by selectively modifying the amino group at the 2-position of chitosan with methyl chloroformate, which was further functionalized with p-methylbenzylamine to produce chitosan (p-methylbenzylurea). Then, the hydroxyl groups at the 3- and 6-positions of the glucose skeleton were modified with various phenyl isocyanates, affording a series of chitosan 3,6-bis(arylcarbamate)-2-(p-methylbenzylurea)s, which were characterized and proposed as chiral selectors for enantiomer separation. Nineteen racemates, most of which are drugs or intermediates for drugs, were selected as the model analytes to evaluate the enantioseparation performance.

The Correlation between the Injury Patterns of the Medial Patellofemoral Ligament in an Acute First-Time Lateral Patellar Dislocation on MR Imaging and the Incidence of a Second-Time Lateral Patellar Dislocation.

Objective: To evaluate the correlation between the injury patterns of the medial patellofemoral ligament (MPFL) on magnetic resonance imaging in an acute first-time lateral patellar dislocation (LPD) and incidence of a second-time LPD.

Materials And Methods: Magnetic resonance images were prospectively analyzed in 147 patients after an acute first-time LPD with identical nonoperative management. The injury patterns of MPFL in acute first-time LPDs were grouped by location and severity for the analysis of the incidence of second-time LPD in a 5-year follow-up.

Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans.

Chitosan bis(phenylcarbamate)-(N-cyclohexylformamide)s and chitosan bis(phenylcarbamate)-(N-hexanamide)s were synthesized as chiral selectors for enantiomeric separation. Since two types of substituents with different structures were, respectively, introduced onto the 2-position and the 3-/6-positions of the glucose skeleton in the chitosans through a "heterogeneous" modification pathway, the enantioseparation performances of the chiral selectors could be improved. Influence of the type and position of the substituents on chiral recognition and enantioseparation abilities was studied in detail, and the structural dependence on enantioseparation performance was particularly demonstrated.

High-performance chiral stationary phases based on chitosan derivatives with a branched-chain alkyl urea.

In this study, two series of chitosan 3,6-bis(arylcarbamate)-2-(isobutylurea)s and corresponding coated-type chiral stationary phases (CSPs) were prepared from two kinds of chitosans with different molecular weights. Most of the prepared CSPs demonstrated better enantioseparation performance than the homemade CSP of cellulose tris(3,5-dimethylphenylcarbamate). The CSPs of chitosan 3,6-bis(4-methylphenylcarbamate)-2-(isobutylurea) with higher molecular weight and chitosan 3,6-bis(3-chloro-4-methylphenylcarbamate)-2-(isobutylurea) with lower molecular weight possessed outstanding chiral recognition abilities which were at least as good as that of the commercialized CSP of Chiralcel OD-H towards the tested chiral analytes.

Structural dependence on the property of chiral stationary phases derived from chitosan bis(arylcarbamate)-(amide)s.

The goal of present study was to investigate the structural dependence of chitosan derivatives on enantioseparation and mobile phase tolerance of the corresponding chiral packing materials for liquid chromatography. Hence, a series of chitosan bis(arylcarbamate)-(n-pentyl amide)s and the related chiral stationary phases (CSPs) were prepared from chitosans with different molecular weights. Because of the H-bond formed via CH-π interaction, the CSP bearing methyl substituent exhibited high tolerance than the ones bearing dichloro substituents.

Enantioseparation characteristics of the chiral stationary phases based on natural and regenerated chitins.

Natural and regenerated chitins were derivatized with 3,5-dimethyphenyl isocyanate. The corresponding chiral stationary phases were prepared by coating the resulting chitin derivatives on 3-aminopropyl silica gel. The swelling capacity of the chitin derivatives, enantioseparation capability, as well as eluents tolerance of the chiral stationary phases were evaluated.

Correlation analysis between injury patterns of medial patellofemoral ligament and vastus medialis obliquus after acute first-time lateral patellar dislocation.

Purpose: To evaluate the correlation between injury patterns of the medial patellofemoral ligament (MPFL) and vastus medialis obliquus (VMO) after acute first-time lateral patellar dislocation (LPD) in adults.

Methods: Magnetic resonance imaging (MRI) was prospectively performed in 132 consecutive adults with acute first-time LPD. Images were acquired and evaluated using standardized protocols.

N-Acylated chitosan bis(arylcarbamate)s: A class of promising chiral separation materials with powerful enantioseparation capability and high eluents tolerability.

In order to comprehensively understand the influence of coordination of the substituent at 2-position with those at 3- and 6-positions on the properties of chitosan derivatives, a series of chitosan 3,6-bis(arylcarbamate)-2-(amide)s (CACAs) and the related chiral stationary phases (CSPs) were prepared and reported in the present study. Specifically, chitosan was N-acylated with carboxylic acid anhydrides, and then further derivatized with various aryl isocyanates to afford CACAs, from which a class of coated-type CSPs were prepared. When the substituent introduced on the acyl group at 2-position and those on the phenyl group of the carbamates at 3- and 6-positions were fittingly combined, these prepared CACAs based CSPs would exhibit powerful chiral recognition ability, further resulting in a class of promising chiral separation materials with excellent enantioseparation performance.

Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography.

The goal of the present work was to study the influence of the swelling of chitosan derivatives on the enantioseparation and the separation performance recovery of chiral stationary phases (CSPs) based on these derivatives. Therefore, six chitosan bis(phenylcarbamate)-(-octyl urea)s were synthesized, which were coated on macroporous 3-aminopropyl silica gel affording new CSPs. Most of the CSPs demonstrated strong enantioseparation capability for the tested chiral compounds.

High performance chiral separation materials based on chitosan bis(3,5-dimethylphenylcarbamate)-(alkyl urea)s.

Enantioseparation plays an important role for many fields and for pharmaceutical industry in particular. Chiral stationary phase (CSP) is the core of chiral liquid chromatography that effectively implements enantioseparation. In order to develop coated type CSPs with excellent enantioseparation capability and high tolerance against mobile phases, in this work, a series of chitosan bis(3,5-dimethylphenylcarbamate)-(alkyl urea)s were synthesized, which were coated on 3-aminopropyl silica gel to afford new CSPs.

Chiral stationary phases based on chitosan bis(4-methylphenylcarbamate)-(alkoxyformamide).

Highly N-deacetylated chitosan was chosen as a natural chiral origin for the synthesis of the selectors of chiral stationary phases. Therefore, chitosan was firstly acylated by various alkyl chloroformates yielding chitosan alkoxyformamides, and then these resulting products were further derivatized with 4-methylphenyl isocyanate to afford chitosan bis(4-methylphenylcarbamate)-(alkoxyformamide). A series of chiral stationary phases was prepared by coating these derivatives on 3-aminopropyl silica gel.

Synthesis of substituted phenylcarbamates of N-cyclobutylformylated chitosan and their application as chiral selectors in enantioseparation.

The goal of this study was to develop new chiral stationary phases (CSPs) with high chiral recognition capability and high compatibility with the so-called "nonstandard solvents". Seven new chitosan bis(phenylcarbamate)-(N-cyclobutylformamide) derivatives were synthesized from chitosan with high degree of deacetylation as a starting material. The corresponding chiral stationary phases (CSPs 1-7) were prepared with the chitosan derivatives as chiral selectors (CSs).

Synthesis and characterization of chitosan alkyl urea.

Chitosan is a versatile material employed for various purposes in many fields including the development of chiral stationary phases for enantioseparation. Chitosan alkyl urea is a kind of intermediate used to prepare enantioseparation materials. In order to synthesize the intermediates, in the present work, a new way to prepare chitosan alkyl urea has been established: chitosan was first reacted with methyl chloroformate yielding N-methoxyformylated chitosan, which was then converted to chitosan alkyl urea through amine-ester exchange reaction.

Data of H/C NMR spectra and degree of substitution for chitosan alkyl urea.

The data shown in this article are related to the subject of an article in Carbohydrate Polymers, entitled "Synthesis and characterization of chitosan alkyl urea" [1]. H NMR and C NMR spectra of chitosan -octyl urea, chitosan -dodecyl urea and chitosan cyclohexyl urea are displayed. The chemical shifts of proton and carbon of glucose skeleton in these chitosan derivatives are designated in detail.

Chiral stationary phases based on chitosan bis(methylphenylcarbamate)-(isobutyrylamide) for high-performance liquid chromatography.

A series of chitosan bis(methylphenylcarbamate)-(isobutyrylamide) derivatives were synthesized by carbamylating chitosan isobutyrylamide with different methylphenyl isocyanates. Then the prepared chitosan derivatives were coated onto 3-aminopropyl silica particles, resulting in a series of new chiral stationary phases (CSPs) for high-performance liquid chromatography. It was observed that the chiral recognition abilities of these coated-type CSPs depended very much on the substituents on the phenyl moieties of the chitosan derivatives, the eluent composition, as well as the structure of racemates.