Category: tetrahydroisoquinoline

Donella-Deana, Arianna; Ruzza, Paolo; Cesaro, Luca; Brunati, Anna Maria; Calderan, Andrea; Borin, Gianfranco; Pinna, Lorenzo A. published an article in FEBS Letters. The title of the article was 《Specific monitoring of Syk protein kinase activity by peptide substrates including constrained analogs of tyrosine》.Quality Control of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:

The ability of Syk protein tyrosine kinase (PTK) to phosphorylate peptides where tyrosine is replaced by conformationally constrained analogs has been exploited to develop highly selective substrates suitable for the specific monitoring of Syk activity. In particular we have synthesized a peptidomimetic, RRRAAEDDE(L-Htc)EEV (syktide), with the 3(S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxyl acid residue (L-Htc) substituted for tyrosine. Although syktide is phosphorylated by Syk with remarkable efficiency (Kcat = 73 min-1, Km = 11 μM), it is not affected to any appreciable extent by a variety of PTKs tested thus far. These properties make syktide the first choice as substrate for the specific monitoring of Syk. 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: 152286-30-1Quality Control 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.Quality Control 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

Computed Properties of C10H11NO3On November 30, 2001 ,《Direct chiral separation of unnatural amino acids by high-performance liquid chromatography on a ristocetin A-bonded stationary phase》 appeared in Chirality. The author of the article were Torok, Gabriella; Peter, Antal; Armstrong, Daniel W.; Tourwe, Drik; Toth, Geza; Sapi, Janos. The article conveys some information:

Direct HPLC chiral separation of numerous underivatized unnatural amino acids on a ristocetin A-bonded chiral stationary phase used in the reversed-phase and in the polar organic chromatog. modes is reported. The effects of different parameters such as mobile phase composition, temperature, and the structure of the analytes on the selectivity in both chromatog. modes are discussed. By variation of the parameters, the separation of the stereoisomers was optimized and, as a result, baseline resolution was achieved in most cases. The experimental process involved the reaction of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Computed Properties 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.Computed Properties 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

Peter, A.; Torok, G.; Toth, G.; Van den Nest, W.; Laus, G.; Tourwe, D.; Armstrong, D. W. published an article in Chromatographia. The title of the article was 《Enantiomeric separation of unusual secondary aromatic amino acids》.Category: tetrahydroisoquinoline The author mentioned the following in the article:

High-performance liquid chromatog. and gas chromatog. methods were developed for the separation of unusual secondary aromatic amino acids. Amino acids containing 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane-1-carboxylic acid and 1,2,3,4-tetrahydro-3-carboxy-2-carboline moieties were synthesized in racemic or chiral forms. The high-performance liquid chromatog. was carried out either on a teicoplanin-containing chiral stationary phase or on an achiral C18 column. In the latter case the diastereomers of the amino acids formed by precolumn derivatization with the chiral reagents 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate or 1-fluoro-2,4-dinitropheny1-5-L-alanine amide were separated The gas chromatog. analyses were based on separation on a Chirasil-L-Val column. 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: 152286-30-1Category: tetrahydroisoquinoline) 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.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

In 2015,PLoS One included an article by Sarkar, Sourav; Pires, Marcos M.. Application In Synthesis of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. The article was titled 《D-Amino acids do not inhibit biofilm formation in Staphylococcus aureus》. The information in the text is summarized as follows:

Bacteria can either exist in the planktonic (free floating) state or in the biofilm (encased within an organic framework) state. Bacteria biofilms cause industrial concerns and medical complications and there has been a great deal of interest in the discovery of small mol. agents that can inhibit the formation of biofilms or disperse existing structures. Herein it was shown that, contrary to previously published reports, D-amino acids do not inhibit biofilm formation of Bacillus subtilis (B. subtilis), Staphylococcus aureus (S. aureus), and Staphylococcus epidermis (S. epidermis) at millimolar concentrations The authors evaluated a diverse set of natural and unnatural D-amino acids and observed no activity from these compounds in inhibiting biofilm formation. In the experimental materials used by the author, we found (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Application In Synthesis 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.Application In Synthesis 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

Recommanded Product: 152286-30-1On March 18, 2008, Liu, Cong; Thomas, James B.; Brieaddy, Larry; Berrang, Bertold; Carroll, F. Ivy published an article in Synthesis. The article was 《An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid》. The article mentions the following:

An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is described wherein a modified Pictet-Spengler reaction was employed to provide 95% yield of the product with 7% racemization or less. The enantiomeric excess of the final product was improved to 99.4% via recrystallization The overall yield of this four-step synthesis provides the title compound in 43% starting from D-tyrosine.(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: 152286-30-1) 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: 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

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

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

Wen, Yabin; Amos, Ruth I. J.; Talebi, Mohammad; Szucs, Roman; Dolan, John W.; Pohl, Christopher A.; Haddad, Paul R. published their research in Analytical Chemistry (Washington, DC, United States) on August 7 ,2018. The article was titled 《Retention Index Prediction Using Quantitative Structure-Retention Relationships for Improving Structure Identification in Nontargeted Metabolomics》.Recommanded Product: 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The article contains the following contents:

Structure identification in nontargeted metabolomics based on liquid-chromatog. coupled to mass spectrometry (LC-MS) remains a significant challenge. Quant. structure-retention relation (QSRR) modeling is a technique capable of accelerating the structure identification of metabolites by predicting their retention, allowing false positives to be eliminated during the interpretation of metabolomics data. 191 Compounds were grouped according to mol. weight and a QSRR study was carried out on the 34 resulting groups to eliminate false positives. Partial least squares (PLS) regression combined with a Genetic algorithm (GA) was applied to construct the linear QSRR models based on a variety of VolSurf+ mol. descriptors. A novel dual-filtering approach, which combines Tanimoto similarity (TS) searching as the primary filter and retention index (RI) similarity clustering as the secondary filter, was used to select compounds in training sets to derive the QSRR models yielding R2 of 0.8512 and an average root mean square error in prediction (RMSEP) of 8.45%. With a retention index filter expressed as ±2 standard deviations (SD) of the error, representative compounds were predicted with >91% accuracy, and for 53% of the groups (18/34), at least one false pos. compound could be eliminated. The proposed strategy can thus narrow down the number of false positives to be assessed in nontargeted metabolomics. In the experiment, the researchers used many compounds, for example, 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3Recommanded Product: 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: 2-Methyl-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

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