Category: 152286-30-1

The author of 《LC enantiomeric separation of unusual amino acids using cyclodextrin-based stationary phases》 were Remsburg, Jeffrey W.; Armstrong, Daniel W.; Peter, Antal; Toth, Geza. And the article was published in Journal of Liquid Chromatography & Related Technologies in 2008. Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:

The use of cyclodextrin based stationary phases was studied for the enantiomeric separation of 20 unusual amino acids. Mobile phase, pH effects, and flow rate were optimized for each separation Separations were limited to aqueous mobile phases. Nineteen of the amino acids were separated, with seven having a resolution ≥1.5. The highest selectivities came from the alpha, acetylated beta, and 2,6-dinitrophenyl-4-trifluoromethylphenyl derivitized beta-cyclodextrin stationary phases. Amino acids containing a 1,2,3,4 tetrahydroisoquinoline carboxylic acid structure showed great compatibility with the acetylated beta-cyclodextrin. Tyrosine analogs, due to lack of retention, were not well suited to the cyclodextrin stationary phases. In addition to this study using (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, there are many other studies that have used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) was used in this study.

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Peter, Antal; Torok, Gabriella; Toth, Geza; Van Den Nest, Wim; Laus, Georges; Tourwe, Dirk published an article on February 27 ,1998. The article was titled 《Chromatographic methods for monitoring the optical isomers of unusual aromatic amino acids》, and you may find the article in Journal of Chromatography A.SDS of cas: 152286-30-1 The information in the text is summarized as follows:

Unusual aromatic amino acids (phenylalanine, tyrosine and tryptophan analogs, and analogs containing tetraline, 1,2,3,4-tetrahydroisoquinoline or 1,2,3,4-tetrahydro-2-carboline skeletons) were synthesized in racemic or chiral form. The enantiomers of these unusual aromatic amino acids were separated by different chromatog. methods. The gas chromatog. analyses were based on separation on a Chirasil-L-Val column, using N-trifluoroacetyl-iso-Bu esters of amino acids, while HPLC was carried out either on a Crownpak CR(+) chiral column, or on an achiral column for the separation of diastereomeric derivatives formed with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide or 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate. In the part of experimental materials, we found many familiar compounds, such as (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1SDS of cas: 152286-30-1)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.SDS of cas: 152286-30-1 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Peter, Antal; Toth, Geza; Olajos, Edit; Fueloep, Ferenc; Tourwe, Dirk published an article in Journal of Chromatography A. The title of the article was 《Monitoring of optical isomers of some conformationally constrained amino acids with tetrahydroisoquinoline or tetraline ring structures. Part II》.Formula: C10H11NO3 The author mentioned the following in the article:

Conformationally constrained amino acids were synthesized in chiral or racemic forms: D- and L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), the erythro-D,L-4-Me analog, D- and L-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, D- and L-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, D,L-2-aminotetraline-2-carboxylic acid, D,L-6-hydroxy-2-aminotetraline-2-carboxylic acid and D,L-6-methoxy-2-aminotetraline-2-carboxylic acid. The optical isomers were characterized and identified by applying precolumn derivatization with chiral reagents (1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate) and enzymic digestion with L-amino acid oxidase, carboxypeptidase A and α-chymotrypsin. The HPLC conditions (pH, eluent composition and different buffers) were varied to obtain optimum separations In the part of experimental materials, we found many familiar compounds, such as (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Formula: C10H11NO3)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Formula: C10H11NO3 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Category: tetrahydroisoquinolineOn October 10, 2014 ,《Direct high-performance liquid chromatographic enantioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior》 was published in Journal of Chromatography A. The article was written by Ilisz, Istvan; Gecse, Zsanett; Pataj, Zoltan; Fulop, Ferenc; Toth, Geza; Lindner, Wolfgang; Peter, Antal. The article contains the following contents:

Two chiral stationary phases containing a quinine- or a quinidine-based zwitterionic ion-exchanger as chiral selector were applied for the enantioseparation of 27 unusual cyclic secondary α-amino acids. The effects of the nature and concentration of the bulk solvent, the acid and base additives, the structures of the analytes and temperature on the enantioresoln. were studied. To study the effects of temperature and to obtain thermodn. parameters, experiments were carried out at constant mobile phase compositions in the temperature range -5 to 55°. The thermodn. parameters indicated that in most cases the separations were enthalpy-driven, but some entropy-driven separations were also observed The sequence of elution of the enantiomers was determined in most cases. In the experiment, the researchers used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Category: tetrahydroisoquinoline)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Category: tetrahydroisoquinoline It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Synthetic Route of C10H11NO3On March 13, 2017, Barnash, Kimberly D.; The, Juliana; Norris-Drouin, Jacqueline L.; Cholensky, Stephanie H.; Worley, Beau M.; Li, Fengling; Stuckey, Jacob I.; Brown, Peter J.; Vedadi, Masoud; Arrowsmith, Cheryl H.; Frye, Stephen V.; James, Lindsey I. published an article in ACS Combinatorial Science. The article was 《Discovery of Peptidomimetic Ligands of EED as Allosteric Inhibitors of PRC2》. The article mentions the following:

The function of EED within Polycomb repressive complex 2 (PRC2) is mediated by a complex network of protein-protein interactions. Allosteric activation of PRC2 by binding of methylated proteins to EED’s aromatic cage is essential for full catalytic activity, but details of this regulation are not fully understood. EED’s recognition of the product of PRC2 activity, histone H3 lysine 27 trimethylation (H3K27me3), stimulates PRC2 methyltransferase activity at adjacent nucleosomes leading to H3K27me3 propagation and, ultimately, gene repression. By coupling combinatorial chem. and structure-based design, we optimized a low affinity methylated Jarid2 peptide to a smaller, more potent peptidomimetic ligand (Kd = 1.14 ± 0.14 μM) of the aromatic cage of EED. Our strategy illustrates the effectiveness of applying combinatorial chem. to achieve both ligand potency and property optimization. Furthermore, the resulting ligands, UNC5114 and UNC5115, demonstrate that targeted disruption of EED’s reader function can lead to allosteric inhibition of PRC2 catalytic activity. In the experimental materials used by the author, we found (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Synthetic Route of C10H11NO3)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Synthetic Route of C10H11NO3 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Albers, Harald M. H. G.; Hendrickx, Loes J. D.; van Tol, Rob J. P.; Hausmann, Jens; Perrakis, Anastassis; Ovaa, Huib published an article in Journal of Medicinal Chemistry. The title of the article was 《Structure-Based Design of Novel Boronic Acid-Based Inhibitors of Autotaxin》.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:

Autotaxin (ATX) is a secreted phosphodiesterase that hydrolyzes the abundant phospholipid lysophosphatidylcholine (LPC) to produce lysophosphatidic acid (LPA). The ATX-LPA signaling axis has been implicated in inflammation, fibrosis, and tumor progression, rendering ATX an attractive drug target. We recently described a boronic acid-based inhibitor of ATX, named HA155 (1). Here, we report the design of new inhibitors based on the crystal structure of ATX in complex with inhibitor 1. Furthermore, we describe the syntheses and activities of these new inhibitors, whose potencies can be explained by structural data. To understand the difference in activity between two different isomers with nanomolar potencies, we performed mol. docking experiments Intriguingly, mol. docking suggested a remarkable binding pose for one of the isomers, which differs from the original binding pose of inhibitor 1 for ATX, opening further options for inhibitor design. In the part of experimental materials, we found many familiar compounds, such as (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn October 31, 1998 ,《A rapid, qualitative thin-layer chromatographic method for the separation of the enantiomers of unusual aromatic amino acids》 appeared in Journal of Planar Chromatography–Modern TLC. The author of the article were Darula, Zsuzsanna; Torok, Gabriella; Wittmann, Gyula; Mannekens, Els; Iterbeke, Koen; Toth, Geza; Tourwe, Dirk; Peter, Antal. The article conveys some information:

A rapid thin-layer chromatog. (TLC) method was developed for the separation and purity control of the enantiomers of several unusual aromatic amino acids (phenylalanine, tyrosine, histidine, and tryptophan analogs, and analogs containing tetralin or 1,2,3,4-tetrahydroisoquinoline skeletons) synthesized in racemic or homochiral form. The compounds were analyzed on Macherey-Nagel Chiralplate TLC plates with acetonitrile-methanol-water, 4 + 1 + 1 or 4 + 1 + 2 (volume/volume) or acetonitrile-methanol-water-diisopropylethylamine, 4 + 1 + 2 + 0.1 (volume/volume) as mobile phase. The compounds were visualized with ninhydrin. Good separation and reliable results were usually obtained. The configurations of the asym. centers of the studied amino acids were determined either using enantiomerically pure amino acids as standards or using enzymes, e.g. α-chymotrypsin, L-amino acid oxidase or carboxypeptidase A. By this method the configurations of unnatural amino acids built into peptides can also be determined after hydrolysis of the peptides. The experimental part of the paper was very detailed, including the reaction process of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Name: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Name: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Reference of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn March 31, 2002, Aires-de-Sousa, Joao; Gasteiger, Johann published an article in Journal of Molecular Graphics & Modelling. The article was 《Prediction of enantiomeric selectivity in chromatography. Application of conformation-dependent and conformation-independent descriptors of molecular chirality》. The article mentions the following:

To process mol. chirality by computational methods and to obtain predictions for properties that are influenced by chirality, a fixed-length conformation-dependent chirality code is introduced. The code consists of a set of mol. descriptors representing the chirality of a 3-dimensional mol. structure. It includes information about mol. geometry and at. properties, and can distinguish between enantiomers, even if chirality does not result from chiral centers. The new mol. transform was applied to two datasets of chiral compounds, each of them containing pairs of enantiomers that had been separated by chiral chromatog. The elution order within each pair of isomers was predicted by Kohonen neural networks (NN) using the chirality codes as input. A previously described conformation-independent chirality code was also applied and the results were compared. In both applications clustering of the two classes of enantiomers (first eluted and last eluted enantiomers) could be successfully achieved by NN and accurate predictions could be obtained for independent test sets. The chirality code described here has a potential for a broad range of applications from stereoselective reactions to anal. chem. and to the study of biol. activity of chiral compounds In the experimental materials used by the author, we found (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Reference of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Reference of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

In 2007,Journal of Liquid Chromatography & Related Technologies included an article by Jiang, C.; Armstrong, D. W.; Lantz, A. W.; Peter, A.; Toth, G.. Formula: C10H11NO3. The article was titled 《Enantiomeric separation of synthetic amino acids using capillary zone electrophoresis》. The information in the text is summarized as follows:

Three chiral selectors, sulfated α-cyclodextrin (SAC), sulfated β-cyclodextrin (SBC), and carboxymethyl β-cyclodextrin (CMBC) were examined as run buffer additives for the separation of sixteen racemic synthetic amino acids and three prepared mixtures of chiral synthetic amino acids, using capillary zone electrophoresis. Seventeen of the nineteen synthetic amino acids were enantiomerically separated and fourteen of them were optimized to baseline using one or more chiral running buffer additives. SAC, with eleven baseline and three partial separations, and SBC, with ten baseline and four partial separations, are more broadly useful than CMBC. Increasing the chiral selector concentration improved the enantioresoln., but also produced longer analyses times. Addition of organic modifier (ethanol) increased migration times and decreased enantiomeric resolution Increasing the pH of the run buffer decreased analyses time as well as resolution Decreasing the applied voltage generally improved resolution After reading the article, we found that the author used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Formula: C10H11NO3)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Formula: C10H11NO3 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem