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Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(S)-2',6'-Dimethyltyrosine hydrochloride is utilized as a key intermediate in the synthesis of innovative therapeutic agents and pharmaceuticals. Its unique structure and properties contribute to the development of new drugs with potential therapeutic benefits.
Used in the Synthesis of Neurotransmitter Modulators:
In the field of neuroscience, (S)-2',6'-Dimethyltyrosine hydrochloride is studied for its potential role in modulating neurotransmitter levels within the brain. This application is significant for understanding and potentially influencing neurochemical processes related to various cognitive functions and neurological conditions.
Used in the Treatment of Neurological Disorders:
(S)-2',6'-Dimethyltyrosine hydrochloride is being investigated for its potential use in the treatment of neurological disorders. Its capacity to modulate neurotransmitter levels suggests that it could be instrumental in managing or alleviating symptoms associated with such disorders, offering new avenues for therapeutic intervention.
Used in Chemical and Biological Assays:
Owing to its stability and water solubility, (S)-2',6'-Dimethyltyrosine hydrochloride serves as a valuable component in various chemical and biological assays. It aids in the testing and analysis of different biological processes and interactions, contributing to a broader understanding of biochemical mechanisms.

Upstream product

• 928138-99-2 (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester; hydrochloride 
• 70547-87-4 2,6-dimethyl-4-hydroxybenzaldehyde 
• 28924-92-7 4-(benzyloxy)-2,6-dimethylbenzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 99953-00-1 (S)-N-Boc-2,6-dimethyltyrosine 
• 81806-45-3 2',6'-dimethyltyrosine 
• 928138-99-2 (R)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester; hydrochloride 

Relevant academic research and scientific papers

A practical and convenient Blanc-type chloromethylation catalyzed by zinc chloride under solvent-free conditions

Chloromethylation of various aromatic hydrocarbons and substituted phenolic derivatives with dimethoxymethane and chlorosulfonic acid was carried out in the presence of 10 mol% of ZnCl2 in a mild and efficient manner under solvent-free conditions. In addition, 2,6-dimethyltyrosine was synthesized in high yield via this protocol.

Solid-Phase Azopeptide Diels-Alder Chemistry for Aza-pipecolyl Residue Synthesis to Study Peptide Conformation

Solid-phase chemistry for the synthesis and Diels-Alder reaction of Fmoc-protected azopeptides has been developed and used to construct aza-pipecolyl (azaPip) peptides. Considering their ability to induce electronic and structural constraints that favor c

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.

Resolution method and application of 6- 2 sphingosahexanoic acid ester (I) as well as preparation method and application thereof (by machine translation)

The preparation method comprises the following steps 2: 6 - 2 preparing the racemic mixture of the dimethyl-L-tyrosine 2 through dynamic kinetic resolution, 6 - and then carrying out 2 dynamic kinetic resolution to obtain the compound salt 6 - of L-tyrosi

Pd-catalyzed dimethylation of tyrosine-derived picolinamide for synthesis of (S)-N-Boc-2,6-dimethyltyrosine and its analogues

A short and efficient synthesis of (S)-N-Boc-2,6-dimethyltyrosine utilizing palladium-catalyzed directed C-H functionalization is described. This represents the first general method for the ortho-dimethylation of tyrosine derivatives and offers a practical approach for preparing this synthetically important building block. Notably, throughout the reaction sequence no racemization occurs at the susceptible a-chiral centers.

Preparation of Constrained Unnatural Aromatic Amino Acids via Unsaturated Diketopiperazine Intermediate

Unnatural aromatic amino acids are useful tools in drug discovery, since their insertion in bioactive peptide sequences can change the side chains spatial orientation, the backbone conformation and above all, their bioactivity. In this communication, we propose a straightforward method to synthesize 2′,6′-dimethyl-tyrosine and 2′,6′-dimehylphenyl-alanine derivatives as handling building blocks for peptide synthesis via unsaturated diketopiperazine (DKP) intermediate.

Convenient, asymmetric synthesis of enantiomerically pure 2',6'- dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine

Asymmetric synthesis of (S)-2',6'-dimethyltyrosine (DMT) via reactions of 4'-benzyloxy-2',6'-dimethylbenzyl bromide with Ni(II)-complexes of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]- benzophenone was developed. Inexpensive and readily available reagents and solvents involved, including recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical yields, make this method synthetically attractive for preparing the target amino acids on a multi-gram scale. (C) 2000 Elsevier Science Ltd.

Process for producing 2,6-disubstituted tyrosine

A process for making 2,6-disubstituted tyrosine by the noble metal coupling of a disubstituted aromatic halide or diazonium salt with an amino-protected 2-aminoacrylic acid to form a (Z)-β-(disubstituted phenyl)-α-acylaminoacrylate, and asymmetrically hydrogenating the acrylate to produce the 2,6-disubstituted tyrosine.