Month: October 2022

Peter, A.; Torok, G.; Armstrong, D. W.; Toth, G.; Tourwe, D. published their research in Journal of Chromatography A on December 22 ,2000. The article was titled 《High-performance liquid chromatographic separation of enantiomers of synthetic amino acids on a ristocetin A chiral stationary phase》.SDS of cas: 152286-30-1 The article contains the following contents:

A macrocyclic glycopeptide, ristocetin A, was used as chiral stationary phase for the HPLC separation of enantiomers of 28 unnatural amino acids, such as analogs of phenylalanine, tyrosine and tryptophan, and analogs containing 1,2,3,4-tetrahydroisoquinoline, tetraline or 1,2,3,4-tetrahydro-2-carboline skeletons. Excellent resolutions were achieved for most of the studied compounds by using reversed-phase or a new polar-organic mobile phase system. The conditions of separation were optimized by variation of the mobile phase composition, temperature and flow-rate. In the experiment, the researchers used (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

Application In Synthesis of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn May 13, 1994 ,《Monitoring of optical isomers of some conformationally constrained amino acids with tetrahydroisoquinoline or tetraline ring structures》 appeared in Journal of Chromatography A. The author of the article were Peter, Antal; Toth, Geza; Tourwe, Dirk. The article conveys some information:

Conformationally constrained amino acids were synthesized in optically pure or racemic forms: D- and L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, its erythro-D,L-4-Me analog, D- and L-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, D- and L-1,2,3,4-tetrahydro-7-hydroxy-6,8-dibromo- and -6,8-diiodoisoquinoline-3-carboxylic acid and D,L-6-hydroxy-2-aminotetraline-2-carboxylic acid. A method was developed for the separation and identification of optical isomers using precolumn derivatization with chiral derivatization reagents: 1-fluoro-2,4-dinitrophenyl-4-L-alaninamide and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate. The effects of pH, eluent composition and different buffers on the separation were also investigated. In the experiment, the researchers used (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

Quality Control of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn March 1, 2002, Peter, Antal; Vekes, Erika; Toth, Geza; Tourwe, Dirk; Borremans, Frans published an article in Journal of Chromatography A. The article was 《Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids》. The article mentions the following:

A new chiral derivatizing agent, (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester, (S)-NIFE, was applied for the HPLC separation of enantiomers of 19 unnatural secondary amino acids: proline, pipecolic acid analogs, piperazine-2-carboxylic acid, morpholine-3-carboxylic acid, thiomorpholine-3-carboxylic acid and analogs containing the 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane, 1,2,3,4-tetrahydro-2-carboline and 2-benzazepine skeletons. Excellent resolutions were achieved for most of the studied compounds by using a reversed-phase mobile phase system. The conditions of separation were optimized by variation of the mobile phase composition 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: 152286-30-1Quality 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

Peter, Antal; Torok, Gabriella; Armstrong, Daniel W. published an article on January 16 ,1998. The article was titled 《High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase》, and you may find the article in Journal of Chromatography A.COA of Formula: C10H11NO3 The information in the text is summarized as follows:

A glycopeptide antibiotic, teicoplanin, was used as chiral stationary phase for the HPLC separation of enantiomers of >30 unnatural amino acids, such as phenylalanine and tyrosine analogs and analogs containing 1,2,3,4-tetrahydroisoquinoline, tetraline, 1,2,3,4-tetrahydro-2-carboline, cyclopentane, cyclohexane, cyclohexene, bicyclo[2.2.1]heptane or heptene skeletons. Excellent resolutions were achieved for most of the studied compounds by using a hydro-organic mobile-phase system. The effects of organic modifier content, temperature and flow-rate on the resolution were studied and the conditions of separation were optimized. In the experiment, the researchers used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1COA of Formula: 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.COA of 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

Peter, Antal; Torok, Gabriella; Toth, Geza; Van Den Nest, Wim; Georges Laus; 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.Recommanded Product: 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. 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: 152286-30-1Recommanded Product: 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.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

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

Shonberg, Jeremy; Draper-Joyce, Christopher; Mistry, Shailesh N.; Christopoulos, Arthur; Scammells, Peter J.; Lane, J. Robert; Capuano, Ben published an article in Journal of Medicinal Chemistry. The title of the article was 《Structure-activity study of N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652), a bitopic ligand that acts as a negative allosteric modulator of the dopamine D2 receptor》.Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride The author mentioned the following in the article:

The authors recently demonstrated that SB269652 I engages one protomer of a dopamine D2 receptor (D2R) dimer in a bitopic mode to allosterically inhibit the binding of dopamine at the other protomer. Herein, the authors investigate structural determinants for allostery, focusing on modifications to three moieties within I. The authors find that orthosteric “”head”” groups with small 7-substituents were important to maintain the limited neg. cooperativity of analogs of I, and replacement of the tetrahydroisoquinoline head group with other D2R “”privileged structures”” generated orthosteric antagonists. Addnl., replacement of the cyclohexylene linker with polymethylene chains conferred linker length dependency in allosteric pharmacol. The authors validated the importance of the indolic NH as a hydrogen bond donor moiety for maintaining allostery. Replacement of the indole ring with azaindole conferred a 30-fold increase in affinity while maintaining neg. cooperativity. Combined, these results provide novel SAR insight for bitopic ligands that act as neg. allosteric modulators of the D2R. In the experiment, the researchers used 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride)

7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride 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