56176-31-9

Usage

Uses

Used in Biochemical Research:
DANSYL-D-PHENYLALANINE FREE ACID is used as a fluorescent probe for studying protein structure, function, and interactions. The fluorescent tag enables researchers to monitor the behavior of proteins in real-time, providing valuable insights into their mechanisms of action and potential applications in drug development.
Used in Drug Development:
DANSYL-D-PHENYLALANINE FREE ACID is used as a precursor in the synthesis of N-sulfonylamino acid derivatives, which have been identified as potential metalloproteinase inhibitors. These inhibitors are of interest in the development of therapeutic agents for the treatment of various diseases, including cancer and neurodegenerative disorders, where metalloproteinases play a crucial role in disease progression.
Used in Diagnostic Applications:
The fluorescent properties of DANSYL-D-PHENYLALANINE FREE ACID make it a valuable tool in the development of diagnostic assays and imaging techniques. Its ability to be detected and quantified in biological samples can aid in the early detection and monitoring of diseases, as well as in the assessment of treatment efficacy.

InChI:InChI=1/C21H22N2O4S/c1-23(2)19-12-6-11-17-16(19)10-7-13-20(17)28(26,27)22-18(21(24)25)14-15-8-4-3-5-9-15/h3-13,18,22H,14H2,1-2H3,(H,24,25)/t18-/m1/s1

Upstream product

• 42808-06-0 N-dansyl-DL-phenylalanine 
• 150-30-1 Phenylalanine 
• 605-65-2 5-(dimethylamino)naphth-1-ylsulfonyl chloride 

Downstream Products

• 76224-06-1 (R)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-phenyl-propionic acid 4-(benzyloxycarbonylamino-imino-methyl)-phenyl ester 

Relevant academic research and scientific papers

Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC

A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.

Enantioselective recognition of a fluorescence-labeled phenylalanine by self-assembled chiral nanostructures

Self-assembled chiral nanostructures such as nanofibers and nanotubes formed by a pyridylpyrazole-conjugated l-glutamide showed an enantioselective recognition toward a fluorescence labeled chiral amino acid.

A new chiral ligand exchange capillary electrophoresis system based on Zn(ii)-l-leucine complexes coordinating with β-cyclodextrin and its application in screening tyrosinase inhibitors

Tyrosinase plays a key role in melanin formation, and it is closely related to hyper pigmentation in animals and enzymatic browning in food. Thus, it is of great significance to screen inhibitors of tyrosinase. In this work, a new chiral ligand exchange-capillary electrophoresis (CLE-CE) system based on the coordination effect of Zn(ii)-l-leucine complexes and β-cyclodextrin (β-CD) was developed for screening the inhibitors of tyrosinase. The effects of the concentration of β-CD, buffer pH, the ratio of l-leucine to Zn(ii), and the complex concentration were investigated with Dns-d,l-tyrosine, Dns-d,l-valine and Dns-d,l-phenylalanine as the tested analytes. The optimum buffer conditions were composed of 100.0 mM boric acid, 5.0 mM ammonium acetate, 3.0 mM Zn(ii), 6.0 mM l-leucine and 4.0 mM β-CD at pH 8.2. It has been found that six pairs of Dns-d,l-AAs could be baseline-separated and five pairs of Dns-d,l-AAs were partly enantioseparated. Then the quantitative analysis of l-tyrosine was conducted and good linearity (r2 = 0.992) was obtained with a concentration ranging from 12.95 μM to 413.3 μM. A kinetics study of tyrosinase was realized, and the Km and Vmax were 636 μM and 312 μmol min-1 mg-1. Moreover, the proposed method was applied in screening the inhibitors of tyrosinase with four kinds of chalcones as the model inhibitors. The results demonstrated that the developed CLE-CE system was favorable for screening enzyme inhibitors, and showed great potential in related drugs discovery and clinical analysis in the future.

Cationic β-cyclodextrin-modified hybrid magnetic microspheres as chiral selectors for selective chiral absorption of dansyl amino acids

Chirally selective functionalized magnetic microspheres show great potential in enantiomeric separations. In this study, a novel class of chiral magnetic selectors was developed by immobilization of vinylimidazolium-β- cyclodextrin chloride (VIMCD-Cl) on 3-methacryloxypropyltrimethoxysilane- modified iron oxide magnetic microspheres through a radical polymerization. The prepared chiral materials have regular three-dimensional core-shell architectures with an average particle size of about 580 nm and a high magnetization saturation of about 51 emu g-1. Fourier transform-infrared spectra (FT-IR), thermogravimetric analysis (TGA) and elemental analysis confirmed that VIMCD-Cl was successfully polymerized on the surface of the magnetic microspheres. The prepared functional magnetic materials were then applied in the selective chiral absorption of three dansyl amino acids using microbatch technology. The results indicated that VIMCD-Cl immobilized magnetic microspheres (VIMCD-MNPs) possessed good enantioselectivities toward the three dansyl amino acids, and showed stronger interactions with the l-enantiomers during the chiral adsorption process. Furthermore, these functionalized chiral magnetic materials possess an excellent recyclability and can be used as effective chiral magnetic selectors for chiral separations.

Clicked AC regioisomer cationic cyclodextrins for enantioseparation

Novel AC regioisomer cationic cyclodextrins have been successfully prepared with azide/alkyne click chemistry. The clicked CDs were explored for the enantioseparation of acidic racemates in capillary electrophoresis.

Enhanced enantioselectivity of molecularly imprinted polymers formulated with novel cross-linking monomers

To enhance the performance of molecularly imprinted polymers (MIPs), three new cross-linking monomers were designed, synthesized, and evaluated as matrix elements for molecularly imprinted polymers. Hybrid cross-linking monomers incorporating methacrylamide/methacrylate (NOBE), vinyl ketone/methacrylamide (NAG), and vinyl ketone/methacrylate (MVK) polymerizable groups, were synthesized and used to prepare MIPs and compared to a traditional MIP formulated with EGDMA. The resulting macroporous MIPs were evaluated by HPLC for their ability to separate the enantiomers of a chiral template. The MIP formulated with the cross-linking monomer NAG showed the highest enantioselectivity and complete baseline resolution for a racemic mixture of the template. Enhancement in selectivity in this MIP may be attributed to the presence of the amide group which can promote hydrogen bonding via favorable 1,3 donor-acceptor interactions with the template, the morphology of the polymeric material obtained due to differences in reactivity between the polymerizable groups and improved resolution in cavity formation as a consequence of shorter cross-linker size.

Analytical- and preparative-scale isoelectric focusing separation of enantiomers

Isoelectric focusing has been used to achieve the analytical- and preparative-scale separation of the enantiomers of amphoteric analytes. By considering the simultaneous multiple equilibria involved in the chiral recognition process, a model has been developed to describe the magnitude of the ΔpI value that develops between the enantiomers in the presence of a noncharged chiral resolving agent, such as a noncharged cyclodextrin. Theoretical analysis of the model indicates that three kinds of IEF enantiomer separations are possible: aniono-selective and cationo-selective, when only the identically charged forms of the enantiomers bind selectively to the resolving agent, and duo-selective, when the differently charged forms of the enantiomers bind selectively to the resolving agent. The model predicts that the ΔpI vs cyclodextrin concentration curves approach limiting ΔpI values which can be as large as 0.1, even when the binding constants of the enantiomers differ only by 10%. The parameters of the model can be readily determined by free solution capillary electrophoretic or pressure- mediated capillary electrophoretic experiments. The validity of the proposed model has been tested with hydroxypropyl β-cyclodextrin as resolving agent and dansyl phenylalanine as probe. Capillary IEF enantiomer separations have been achieved using both ampholytes and binary propionic acid-serine buffers (Bier's buffers). Preparative-scale IEF enantiomer separations with production rates as high as 1.3 mg/h have been achieved in an Octopus continuous free-flow electrophoretic system.

Chiral separation of enantiomers of amino acid derivatives by HPLC on vancomycin and teicoplanin chiral stationary phases

The chiral separation of α-amino acids by liquid chromatography using macrocyclic antibiotic bonded stationary phases were studied. Teicoplanin and vancomycin bonded stationary phases have been used to separate enantiomers of dansyl amino acids in the reversed - phase high performance liquid chromatography mode. By comparison of chromatographic parameters obtained by use of both chiral stationary phases it the mechanism of chiral separation could be suggested. The better separation - greater value of R(j,i) of enantiomers - was achieved by the teicoplanin column.

Direct resolution of optically active isomers on chiral packings containing ergoline skeletons. 5. Enantioseparation of amino acid derivatives

A new procedure for ergot alkaloid-based chiral stationary phase preparation is described. Synthesis is based on bonding the allyl derivative of terguride to mercaptopropylsilanized silica gel. The packing exhibits higher content of chiral selector, stability, reproducibility, and enantioselectivity toward amino acids compared to that previously studied. The chromatographic behavior of amino acids with different side chains and substituent groups is investigated in order to obtain a deeper insight into the enantiodiscriminative mechanism as well as to determine the limitations and strengths of terguride as a chiral selector for this class of compounds. A variety of factors, including mobile phase parameters such as pH, ionic strength, content and nature of organic modifier, and temperature, are examined. A new procedure for ergot alkaloid-based chiral stationary phase preparation is described. Synthesis is based on bonding the allyl derivative of terguride to mercaptopropylsilanized silica gel. The packing exhibits higher content of chiral selector, stability, reproducibility, and enantioselectivity toward amino acids compared to that previously studied. The chromatographic behavior of amino acids with different side chains and substituent groups is investigated in order to obtain a deeper insight into the enantiodiscriminative mechanism as well as to determine the limitations and strengths of terguride as a chiral selector for this class of compounds. A variety of factors, including mobile phase parameters such as pH, ionic strength, content and nature of organic modifier, and temperature, are examined.

Enantiomeric Separation with Use of Stationary Phase Coated with Micellar Bile Salt for Microcolumn Liquid Chromatography

A novel method for enantiomeric separation using an ODS stationary phase coated with bile salt micelles in high-performance liquid chromatography has been developed, where bile salt surfactants such as sodium cholate and sodium deoxycholate were used for micelle formation.The present method was applied to the separation of the enantiomers of 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (BNDHP) and N-dansylphenylalanine by using acetonitrile-water solution as the mobile phase.The dependence of the capacity factors and separation factors on the acetonitrile concentration in the mobile phase was examined for BNDHP enantiomers.These factors decreased with increasing acetonitrile concentration, which resulted in the change of separation characteristics of BNDHP enantiomers.Although BNDHP and N-dansylphenylalanine enantiomers were separated, similar enantiomers such as 2,2'-dihydroxy-1,1'-binaphthyl and other N-dansylamino acids were not separated in the present separation system.