5796-17-8

Usage

Uses

Used in Pharmaceutical Industry:
D-DOPA is used as an impurity in the production of L-DOPA, which is a crucial medication for the treatment of Parkinson's disease. The presence of D-DOPA as an impurity can affect the efficacy and safety of L-DOPA, making it important to control its levels during the manufacturing process.
Used in Research and Development:
D-DOPA is used as a research compound for studying the differences between enantiomers and their effects on biological systems. Understanding the properties and behavior of D-DOPA can contribute to the development of new drugs and therapies, as well as improve the understanding of stereochemistry in pharmaceuticals.
Used in Quality Control:
D-DOPA is used in the quality control of L-DOPA products to ensure that the enantiomeric purity meets the required standards. This is essential for maintaining the safety and effectiveness of L-DOPA medications, as the presence of D-DOPA can potentially impact the therapeutic outcomes for patients with Parkinson's disease.

Biochem/physiol Actions

DOPA enantiomer that lacks biological activity.

InChI:InChI=1/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m1/s1

Upstream product

• 19641-90-8 N-acetyl-3,4-dihydroxy-D-phenylalanine 
• 59624-86-1 (R)-1,1-dimethylethyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate 
• 7101-51-1 (+/-)-3-(3,4-dihydroxyphenyl)-2-methyl-DL-alanine 
• 148806-54-6 3-(3,4-dimethoxyphenyl)alanine ethyl ester 
• 33605-56-0 (R)-2-amino-3-(3,4-dimethoxyphenyl)propanoic acid 
• 88425-33-6 (S)-α-(N-(phenylsulfonyl)amino)-β-hydroxy-3,4-dimethoxypropiophenone 
• 88425-39-2 (R)-2-(N-(phenylsulfonyl)amino)-1-hydroxy-3-(3,4-dimethoxyphenyl)propane 
• 2859-78-1 4-Bromoveratrole 
• 13250-12-9 (R)-sec-butylamine 
• 513-49-5 (S)-2-aminobutane 
• 345896-50-6 (R)-1,1-dimethylethyl 2-amino-3-(3,4-methylenedioxyphenyl)propanoate 
• 71855-43-1 (R)-(3,4-dihydroxyphenyl)alanine methyl ester 
• 88425-44-9 (R)-2-(N-(phenylsulfonyl)amino)-3-(3,4-dimethoxyphenyl)propionic acid 
• 63-84-3 dopa 

Downstream Products

• 13520-94-0 Dopachrome 
• 55136-58-8 5-S-G-D-D 
• 167569-09-7 6-[18F]fluoro-D-3,4-dihydroxy phenylalanine 
• 618461-00-0 N-methyl-3,4-dihydroxyphenyl-D-alanine methyl ester 
• 618460-97-2 3-(3,4-dihydroxy-phenyl)-(R)-2-[3-trans-(3,4-dihydroxy-phenyl)-thioacryloylamino]-propionic acid methyl ester tetra(t-butyl dimethylsilyl)ether 
• 618460-96-1 N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether 
• 240428-61-9 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-(4-methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-hydroxy-D-tyrosine 
• 618460-38-1 D-clovamide methyl ester 
• 889133-43-1 methyl (R)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochloride salt 
• 19641-90-8 N-acetyl-3,4-dihydroxy-D-phenylalanine 
• 117831-98-8 (R)-3-(2-Fluoro-4,5-dimethoxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid ethyl ester 
• 97731-03-8 6-fluoro-D-DOPA 

Relevant academic research and scientific papers

Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography

Separation of racemic mixtures is of great importance and interest in chemistry and pharmacology. Porous materials including metal-organic frameworks (MOFs) have been widely explored as chiral stationary phases (CSPs) in chiral resolution. However, it remains a challenge to develop new CSPs for reversed-phase high-performance liquid chromatography (RP-HPLC), which is the most popular chromatographic mode and accounts for over 90% of all separations. Here we demonstrated for the first time that highly stable Zr-based MOFs can be efficient CSPs for RP-HPLC. By elaborately designing and synthesizing three tetracarboxylate ligands of enantiopure 1,1′-biphenyl-20-crown-6, we prepared three chiral porous Zr(IV)-MOFs with the framework formula [Zr6O4(OH)8(H2O)4(L)2]. They share the same flu topological structure but channels of different sizes and display excellent tolerance to water, acid, and base. Chiral crown ether moieties are periodically aligned within the framework channels, allowing for stereoselective recognition of guest molecules via supramolecular interactions. Under acidic aqueous eluent conditions, the Zr-MOF-packed HPLC columns provide high resolution, selectivity, and durability for the separation of a variety of model racemates, including unprotected and protected amino acids and N-containing drugs, which are comparable to or even superior to several commercial chiral columns for HPLC separation. DFT calculations suggest that the Zr-MOF provides a confined microenvironment for chiral crown ethers that dictates the separation selectivity.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

The preparation method of the levodopa intermediate derivatives

The invention relates to a preparation method for a levodopa intermediate derivative. The preparation method comprises: in a solvent, reacting 3, 4-dimethoxybenzene phenylalanine shown as formula I with (+)-tartaric acid derivative to obtain the salt of a [(-)-3, 4-dimethoxybenzene phenylalanine]2.(+)- tartaric acid derivative. The solvent includes an alcohol solvent and an ester solvent. The racemization method includes: in the solvent, under the action of an aldehyde or ketone catalyst, reacting the 3, 4-dimethoxybenzene phenylalanine shown as formula I at 0-90DEG C for 0.5-24 h. The preparation method for the levodopa intermediate derivative provided by the invention has simple steps, and the prepared enantiomer has high purity and is low in cost, thus being applicable to industrial production. (reaction formula).

Chiral ligand-exchange resolution of underivatized amino acids on a dynamically modified stationary phase for RP-HPTLC

The synthesis of Spi(τ-dec), derived from the selective alkylation of L-spinacine (4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid) at the τ-nitrogen of its heteroaromatic ring, with a linear hydrocarbon chain of 10 carbon atoms, is described here for the first time. Spi(τ-dec) was successfully employed in the past to prepare home-made chiral columns for chiral ligand-exchange high-performance liquid chromatography. In the present article a new method is described, using Spi(τ-dec) as a chiral selector in high-performance thin-layer chromatography (HPTLC): commercial hydrophobic plates were first coated with Spi(τ-dec) and then treated with copper sulfate. The performance of this new chiral stationary phase was tested against racemic mixtures of aromatic amino acids, after appropriate optimization of both the conditions of preparation of the plates and the mobile phase composition. The enantioselectivity values obtained for the studied compounds were higher than those reported in the literature for similar systems. The method employed here for the preparation of chiral HPTLC plates proved practical, efficient, and inexpensive. Chirality 26:313-318, 2014. 2014 Wiley Periodicals, Inc.

SEPARATING AGENT FOR CHROMATOGRAPHY

A separating agent for chromatography is provided that is useful for the separation of specific compounds, e.g., for the optical resolution of amino acids. This separating agent for chromatography provides a higher productivity and contains a crown ether-like cyclic structure and optically active binaphthyl. This separating agent for chromatography containing a crown ether-like cyclic structure and optically active binaphthyl is provided by introducing a substitution group for binding to carrier into a specific commercially available 1,1′-binaphthyl derivative that has substituents at the 2, 2′, 3, and 3′ positions, then introducing a crown ether-like cyclic structure, and subsequently chemically bonding the binaphthyl derivative to the carrier through the substitution group for binding to carrier.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Stereospecificity of mushroom tyrosinase immobilized on a chiral and a nonchiral support

Mushroom tyrosinase was immobilized from an extract onto glass beads covered with the cross-linked totally cinnamoylated derivates of D-sorbitol (sorbitol cinnamate) and glycerine (glycerine cinnamate). The enzyme was immobilized onto the support by direct adsorption, and the quantity of immobilized tyrosinase was higher for sorbitol cinnamate, the support with the higher number of esterified hydroxyls per unit of monosacharide, than for glycerine cinnamate. The results obtained from the stereospecificity study of the monophenolase and diphenolase activity of immobilized mushroom tyrosinase are reported. The enantiomers L-tyrosine, DL-tyrosine, D-tyrosine, L-dopa, DL-dopa, D-dopa, L-α-methyldopa, DL-α-methyldopa, L-isoprenaline, DL-isoprenaline, L-adrenaline, DL-adrenaline, L-noradrenaline, and D-noradrenaline were assayed with tyrosinase immobilized on a chiral support (sorbitol cinnamate), whereas L-tyrosine, DL-tyrosine, D-tyrosine, L-dopa, DL-dopa, D-dopa, L-α-methyldopa, and DL-α-methyldopa were assayed with tyrosinase immobilized on a nonchiral support (glycerine cinnamate). The same Vmaxapp values for each series of enantiomers were obtained. However, the Kmapp values were different, the L isomers showing lower values than the DL isomers, whereas the highest K mapp value was obtained with D isomers. No difference was observed in the stereospecificity of tyrosinase immobilized on a chiral (sorbitol cinnamate) or nonchiral (glycerine cinnamate) support.

Cavity effects on the enantioselectivity of chiral amido[4]resorcinarene stereoisomers

The dramatic effects of the size and hydrophilic/hydrophobic properties of cavities on the intrinsic reaction kinetics and dynamics is shown by the gas-phase reaction of (R)-(-)-2-butylamine and complexes of stereoisomeric amido[4]resorcinarene hosts with aromatic amino acids. The graph shows the kinetic plots of the base-induced loss of L-Phe (green), L-Tyr (red), and L-dopa (blue).