29588-07-6

Usage

Uses

Used in Laboratory Analysis:
PTH-Phe is used as a derivatizing agent for amino acids, specifically for the detection and quantification of phenylalanine in biological samples. Its high stability and sensitivity make it an ideal choice for chromatographic and mass spectrometric analysis, ensuring accurate and reliable results.
Used in Diagnostic Applications:
In the medical field, PTH-Phe plays a crucial role in the diagnosis and monitoring of phenylketonuria (PKU), a genetic disorder characterized by the accumulation of phenylalanine in the body. By facilitating the specific detection of phenylalanine, PTH-Phe aids in the early identification and management of PKU, helping to prevent its associated complications.
Used in Pharmaceutical Industry:
PTH-Phe is also employed in the development and quality control of pharmaceutical products, particularly those containing phenylalanine as an active ingredient or excipient. Its ability to accurately quantify phenylalanine levels ensures the safety and efficacy of these medications.
Used in Research and Development:
In the realm of scientific research, PTH-Phe serves as a valuable tool for studying the role of phenylalanine in various biological processes and its interaction with other molecules. This knowledge can contribute to the development of new therapeutic strategies and a deeper understanding of amino acid metabolism.

InChI:InChI=1/C16H14N2OS/c19-15-14(11-12-7-3-1-4-8-12)17-16(20)18(15)13-9-5-2-6-10-13/h1-10,14H,11H2,(H,17,20)/t14-/m0/s1

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 63-91-2 L-phenylalanine 
• 15028-44-1 DL-phenylalanine methyl ester 
• 154738-10-0 N-phenyl-N'-(2-phenyl-1-carboxyethyl)thiocarbamide 
• 35661-40-6 N-Fmoc L-Phe 
• 49645-33-2 phenyl thioisocyanate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 62-53-3 aniline 
• 51034-34-5 potassium aniline dithiocarbamate 
• 1219278-46-2 BF₄^(1-)*C₂₈H₃₀N₅OS⁽¹⁺⁾ 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 74734-11-5 1H-imidazole-1-carbodithioic acid methyl ester 
• 150-30-1 Phenylalanine 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 

Downstream Products

• 32832-07-8 (E)-5-benzylidene-3-phenyl-2-thioxoimidazolidin-4-one 
• 1393347-01-7 (Z)-4-benzylidene-1-phenyl-1H-imidazol-5-one 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 155496-29-0 2-thioxo-3-phenyl-5-phenylmethylene-4-imidazolidinone 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 716-79-0 2-phenyl-1H-benzoimidazole 

Relevant academic research and scientific papers

Base controlled three-component regioselective synthesis of 2-imino thiazolines and 2-thioxoimidazolin-4-ones

Base-controlled regioselective synthesis of 2-imino thiazolines and 2-thioxoimidazolin-4-ones was achieved to use a one-pot reaction between chiral amino esters, isothiocyanates, and α-bromoketones/alkyl halides. This three-component coupling reaction in acetonitrile provides 2-imino thiazolines, whereas the formation of 2-thioxoimidazolin-4-ones was observed under basic conditions at ambient temperature. The corresponding products were obtained in good to excellent yield with broad substrate scope. Isolation of thiourea and thiohydantoin intermediates disclosed the course of the reaction mechanism.

Microwave-assisted traceless synthesis of thiohydantoin

An efficient, microwave-assisted method for the liquid-phase combinatorial synthesis of 3,5-disubstituted-thiohydantoin has been developed. Fmoc-protected amino acids were coupled with HO-PEG-OH and after deprotection, reacted with various isothiocyanates

Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light-Mediated Antibacterial Activity

Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco-friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light.

Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes

A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface (B3LYP/6–31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.

Enantioselective Synthesis of 5,5-Disubstituted Hydantoins by Br?nsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template

A new method for the enantioselective synthesis of 5,5-disubstituted (quaternary) hydantoins was developed on the basis of an organocatalytic Michael reaction approach involving the use of 2-benzylthio-3,5-dihydroimidazol-4-ones as key hydantoin surrogates. The method is general with respect to the substitution pattern at the hydantoin N1 (alkyl, aryl, acyl), N3 (aryl), and C5 (linear/branched alkyl, aryl) positions and affords essentially single diastereomeric products with enantioselectivities higher than 95 % ee in most cases. Among the bifunctional Br?nsted base/H-bond catalysts examined, a known squaramide–tertiary amine catalyst and a newly prepared squaramide–tertiary amine catalyst provide the highest selectivity so far with either nitroolefins or vinyl ketones as the acceptor components. Kinetic measurements support a first-order rate dependence on both reaction partners, the donor template and the Michael acceptor, whereas competitive 1H NMR spectroscopy experiments reveal the high ability of the template for catalyst binding.

NOVEL AZULENYL COMPOUND

PROBLEM TO BE SOLVED: To provide: a method for determining amino acid sequences such as trace peptides and proteins; as well as a compound that can be used as an Edman reagent suitable for said method, specifically a compound that has a high UV absorbance and efficiently reacts with peptides. SOLUTION: Provided is an azulenyl isothiocyanate compound represented by the formula (1). (Each R independently is a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group or heteroaryl group having 6 to 10 carbon atoms; n is an integer from 0 to 7; in particular, R preferably is an alkyl group having 1 to 10 carbon atoms, and further preferably has substituent group at 1 or more of the carbon 3-, 5-, 8-position.). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

New functionalized 8-hydroxyquinoline-5-sulfonic acid mesoporous silica (HQS-SBA-15) as an efficient catalyst for the synthesis of 2-thiohydantoin derivatives

Mesoporous silica SBA-15 functionalized with 8-hydroxyquinoline-5-sulfonic acid (HQS-SBA-15) was used as a new recyclable nanocatalyst for the one-pot synthesis of 2-thiohydantoin derivatives under solvent-free conditions. The catalyst exhibited excellent recyclability at least for 3 times with a high catalytic activity.

Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins

A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.

Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives from S -Amino Acids and Phenylisothiocyanate in et 3N/DMF-H 2O

A concise approach for the transformation of various S-amino acids into the 5-alkyl-3-phenyl-2-thioxoimidazolidin-4-one heterocycles using phenylisothiocyanate is described. Phenylthiohydantoins of amino acid were synthesized at room temperature in Et3N/DMF-H2O with easy workup and excellent yields.

Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary

Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values.