3417-91-2

Usage

Chemical Properties

Crystalline

InChI:InChI=1/C10H13NO3.ClH/c1-14-10(13)9(11)6-7-2-4-8(12)5-3-7;/h2-5,9,12H,6,11H2,1H3;1H/t9-;/m0./s1

Upstream product

• 67-56-1 methanol 
• 60-18-4 L-tyrosine 
• 77-76-9 2,2-dimethoxy-propane 
• 3978-80-1 Boc-Tyr-OH 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 74-88-4 methyl iodide 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 
• 946-80-5 (benzyloxy)benzene 
• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 3417-91-2 tyrosine methyl ester hydrochloride 
• 556-02-5 ?Tyr 
• 16870-43-2 L-tyrosine hydrochloride 
• 142847-18-5 N-(tert-butoxycarbonyl)tyrosine 

Downstream Products

• 4985-46-0 L-Tyr-NH₂ 
• 101575-09-1 N-benzoyl-L-tyrosine methylamide 
• 3641-25-6 N-tert-Pentyloxycarbonyl-L-tyrosin 
• 15149-72-1 N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosine methyl ester 
• 19391-50-5 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-(4-hydroxyphenyl)propanoate 
• 18658-65-6 N-tret-butoxycarbonyl-L-leucinyl-L-tyrosine methyl ester 
• 3799-87-9 methyl (2,2,2-trifluoroacetyl)-L-tyrosinate 
• 30782-90-2 N-decanoyl-L-tyrosine methyl ester 
• 65160-62-5 N^α-t-butyloxycarbonyl-glycyl-L-tyrosine methyl ester 
• 83851-79-0 (5-bromo-2-thenoyl)-L-Tyr-OMe 
• 139455-99-5 (S)-3-Acetyl-1-(4-chloro-phenyl)-5-(4-hydroxy-benzyl)-4,5-dihydro-1H-[1,2,4]triazin-6-one 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 24118-03-4 Z-L-Ser-L-Tyr-OMe 
• 28252-46-2 Z-L-Tyr-L-Tyr-OMe 

Relevant academic research and scientific papers

SYHTHESIS OF 2- AND 3-FLUOROTYROSINE WITH DILUTE FLUORINE GAS

Differences in reactivity and selectivity of fluorine gas towards L-tyrosine and the O,N-diacetylated derivative of L-tyrosine methyl ester have been exploited for the synthesis of 2- and 3-fluorotyrosine.Both 2- and 3-fluorotyrosine were identified by 2H, 19F and 13C NMR spectroscopy and high resolution mass spectrometry.The short synthesis time and high reaction yields allow this procedure to be used for the incorporation of the short lived positron emitting radionuclide 18F into the aromatic ring of L-tyrosine.

Polystyrene or Magnetic Nanoparticles as Support in Enantioselective Organocatalysis? A Case Study in Friedel-Crafts Chemistry

Heterogenized versions of the second-generation MacMillan imidazolidin-4-one are described for the first time. This versatile organocatalyst has been supported on 1% DVB Merrifield resin and Fe3O4 magnetic nanoparticles through a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. The resulting catalytic materials have been successfully applied to the asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes. While both catalytic systems can be easily recovered and admit repeated recycling, the polystyrene-based catalyst shows higher stability and provides better stereoselectivities.

RETRACTED ARTICLE: Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrug of 5-aminosalicylic acid for colon-specific drug delivery in inflammatory bowel disease

Mutual azo prodrug of 5-aminosalicylic acid with l-tyrosine was synthesized by coupling l-tyrosine with salicylic acid, for targeted drug delivery to the inflamed gut tissue in inflammatory bowel disease. The structure was confirmed by elemental analysis, IR and NMR spectroscopy. In vitro kinetic studies in rat fecal matter showed 87.18% release of 5-aminosalicylic acid with a half-life of 140.28 min, following first order kinetics. Therapeutic efficacy of the carrier system and the mitigating effect of the azo conjugate were evaluated in trinitrobenzenesulfonic acid-induced experimental colitis model. Myeloperoxidase activity was determined by the method of Krawisz et?al. The synthesized prodrug was found to produce comparable mitigating effect as that of sulfasalazine on colitis in rats.

Enhancement of the Anti-Inflammatory Activity of NSAIDs by Their Conjugation with 3,4,5-Trimethoxybenzyl Alcohol

The synthesis of derivatives of three nonspecific COX-1 and COX-2 inhibitors, ibuprofen, ketoprofen, naproxen is presented. These acids were connected via an amide bond with an amino acid (L-proline, L-tyrosine, and beta-alanine) used as a linker. The amino acid carboxylic group was esterified with 3,4,5 trimethoxybenzyl alcohol. The activity of the novel derivatives was examined in vivo on carrageenan-induced inflammation, and in vitro, as cyclooxygenase and lipoxygenase inhibitors. It was found that the new compounds were more potent anti-inflammatory agents than the parent drugs. Thus, the ibuprofen (21) and ketoprofen (16) derivatives reduced rat paw edema by 67 and 91% (the reduction by the relevant NSAIDs was 36 and 47%, respectively). They inhibited COX-2 more than the starting drugs (21 by 67%, ibuprofen 46%, 19 by 94%, ketoprofen 49%). Docking of compounds on the active sites of COX-1 and COX-2 reflects their in vitro activity. Thus, 19 adopts an unfavorable orientation for COX-1 inhibition, but it binds effectively in the binding pocket of COX-2, in agreement with the absence of activity for COX-1 and the high inhibition of COX-2. In conclusion, the performed structural modifications result in the enhancement of the anti-inflammatory activity, compared with the parent NSAIDs.

PROCESS FOR MAKING BIARYL-BRIDGED CYCLIC PEPTIDES

The invention provides a method of preparing a biaryl-bridged cyclic peptide compound of Formula (I), where R1, R2, R3, R4, R5, R8, R7, R8, R9, R10, R11, R12, n and m are as defined in the specification. The biaryl-bridged cyclic peptides of Formula (I) are used in the preparation of pharmaceutically active substances, such as, for example, arylomycin and arylomycin analogues.

Preparation method of L-tyrosine derivative

The invention discloses a preparation method of an L-tyrosine derivative. The L-tyrosine derivative is O-alkyl-N-[fluorenylmethoxycarbonyl]-L-tyrosine, L-tyrosine is used as a starting material, the O-alkyl-N-[fluorenylmethoxycarbonyl]-L-tyrosine is prepared through esterification, amidation, etherification/hydrolysis and amidation in sequence, the total yield of the target product can reach 61.5%, and the ee value can reach 99% or above. The preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, lower cost and the like, for example, separation of triphenylphosphine oxide is avoided through etherification reaction. The method has the advantages of simple process, short route, mild reaction conditions and the like, for example, etherification and hydrolysis adopt a one-pot method; and the whole technological process generates few three wastes, the product yield and purity are high, and the method is suitable for industrial production.

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Transition-metal ion-mediated morphological transformation of pyridine-based peptide nanostructures

Inspired by natural metallopeptides, we have rationally designed two pyridine-conjugated short peptides. These two peptide conjugates formed a pair of constitutional isomers that helped us describe their structure-function relationship. Both the isomers consisted of an equal number of aromatic amino acid residues, but shuffling was observed in the position of two key amino acids, viz; tyrosine and phenylalanine, which brought a remarkable change in their self-assembling behavior. The presence of specific functional groups and chemical diversity in both conjugates made them very active towards metal coordination. Both the constitutional isomers adopted different pathways of self-assembly, which could be further controlled or transformed by the use of transition metal ions. Interestingly, it was observed that the metal ions could precisely control the morphology of these metallopeptide nanostructures and make them more stable. Therefore, such artificial metallopeptides possess remarkable advantages over the natural counterparts primarily due to their tailor-made chemical structures.

Tyrosine-Specific Modification via a Dearomatization-Rearomatization Strategy: Access to Azobenzene Functionalized Peptides

Azobenzene functionalized peptides are of great importance in photoresponsive biosystems and photopharmacology. Herein, we report an efficient approach to prepare azobenzene functionalized peptides through late-stage modification of tyrosine-containing peptides using a dearomatization-rearomatization strategy. This approach shows good chemoselectivity and site selectivity as well as sensitive group tolerance to various peptides. This method enriches the postsynthetic modification toolbox of peptides and has great potential to be applied in medicinal chemistry and chemical biology.

Novel Mixed NOP/Opioid Receptor Peptide Agonists

The nociceptin/orphanin FQ (N/OFQ)/N/OFQ receptor (NOP) system controls different biological functions including pain and cough reflex. Mixed NOP/opioid receptor agonists elicit similar effects to strong opioids but with reduced side effects. In this work, 31 peptides with the general sequence [Tyr/Dmt1,Xaa5]N/OFQ(1-13)-NH2 were synthesized and pharmacologically characterized for their action at human recombinant NOP/opioid receptors. The best results in terms of NOP versus mu opioid receptor potency were obtained by substituting both Tyr1 and Thr5 at the N-terminal portion of N/OFQ(1-13)-NH2 with the noncanonical amino acid Dmt. [Dmt1,5]N/OFQ(1-13)-NH2 has been identified as the most potent dual NOP/mu receptor peptide agonist so far described. Experimental data have been complemented by in silico studies to shed light on the molecular mechanisms by which the peptide binds the active form of the mu receptor. Finally, the compound exerted antitussive effects in an in vivo model of cough.