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123715-02-6,MFCD06659984
Catalog No.:AA000KWX

123715-02-6 | 2,6-Dimethyl-l-tyrosine

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100mg
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250mg
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1g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA000KWX
Chemical Name:
2,6-Dimethyl-l-tyrosine
CAS Number:
123715-02-6
Molecular Formula:
C11H15NO3
Molecular Weight:
209.2417
MDL Number:
MFCD06659984
SMILES:
OC(=O)[C@H](Cc1c(C)cc(cc1C)O)N
Properties
Computed Properties
 
Complexity:
220  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
-1  

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,1992,vol.35,p.223-233

[2]Patent:WO2016/144905,2016,A1.Locationinpatent:Paragraph0156

[1]Synthesis,1992,p.741-743

123715-02-6    543-27-1   
C16H23NO5 

[1]JournalofMedicinalChemistry,1992,vol.35,p.223-233

[1]JournalofMedicinalChemistry,1997,vol.40,p.3100-3108

[2]BioorganicandMedicinalChemistryLetters,2005,vol.15,p.599-602

[3]Organicprocessresearchanddevelopment,2011,vol.15,p.1124-1129

[1]BioorganicandMedicinalChemistryLetters,2005,vol.15,p.599-602

Literature

Title: Characterization of antinociceptive potency of endomorphin-2 derivatives with unnatural amino acids in rats.

Journal: Acta physiologica Hungarica 20120901

Title: Bifunctional μ/δ opioid peptides: variation of the type and length of the linker connecting the two components.

Journal: Chemical biology & drug design 20120201

Title: In vivo antinociception of potent mu opioid agonist tetrapeptide analogues and comparison with a compact opioid agonist-neurokinin 1 receptor antagonist chimera.

Journal: Molecular brain 20120101

Title: Lipo-endomorphin-1 derivatives with systemic activity against neuropathic pain without producing constipation.

Journal: PloS one 20120101

Title: Effect of 2',6'-dimethyl-L-tyrosine (Dmt) on pharmacological activity of cyclic endomorphin-2 and morphiceptin analogs.

Journal: Bioorganic & medicinal chemistry 20111201

Title: Discovery of a potent and efficacious peptide derivative for δ/μ opioid agonist/neurokinin 1 antagonist activity with a 2',6'-dimethyl-L-tyrosine: in vitro, in vivo, and NMR-based structural studies.

Journal: Journal of medicinal chemistry 20110414

Title: Role of 2',6'-dimethyl-l-tyrosine (Dmt) in some opioid lead compounds.

Journal: Bioorganic & medicinal chemistry 20100815

Title: N-methylated cyclic enkephalin analogues retain high opioid receptor binding affinity.

Journal: Chemical biology & drug design 20100201

Title: Delta opioid receptor on equine sperm cells: subcellular localization and involvement in sperm motility analyzed by computer assisted sperm analyzer (CASA).

Journal: Reproductive biology and endocrinology : RB&E 20100101

Title: Cyclic opioid peptide agonists and antagonists obtained via ring-closing metathesis.

Journal: Chemical biology & drug design 20091001

Title: [Overview in 45 years of studies on peptide chemistry].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20091001

Title: Biological activity of endomorphin and [Dmt1]endomorphin analogs with six-membered proline surrogates in position 2.

Journal: Bioorganic & medicinal chemistry 20090601

Title: Novel opioid peptide derived antagonists containing (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp].

Journal: Journal of medicinal chemistry 20080925

Title: Conformation-activity relationships of cyclo-constrained micro/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin.

Journal: Journal of peptide science : an official publication of the European Peptide Society 20080801

Title: Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides.

Journal: Bioorganic & medicinal chemistry 20080601

Title: Targeting mitochondria.

Journal: Accounts of chemical research 20080101

Title: Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform.

Journal: Bioorganic & medicinal chemistry letters 20071101

Title: [N-allyl-Dmt1]-endomorphins are micro-opioid receptor antagonists lacking inverse agonist properties.

Journal: The Journal of pharmacology and experimental therapeutics 20071001

Title: Novel diastereomeric opioid tetrapeptides exhibit differing pharmacological activity profiles.

Journal: Brain research bulletin 20070914

Title: Bioactivity of new mu and delta opioid peptides.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20070901

Title: Bifunctional [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed mu-agonist/delta-antagonist and dual mu-agonist/delta-agonist opioid ligands.

Journal: Journal of medicinal chemistry 20070614

Title: Comparison of the in vitro apparent permeability and stability of opioid mimetic compounds with that of the native peptide.

Journal: Bioorganic & medicinal chemistry letters 20070401

Title: Synthesis and characterization of potent and selective mu-opioid receptor antagonists, [Dmt(1), D-2-Nal(4)]endomorphin-1 (Antanal-1) and [Dmt(1), D-2-Nal(4)]endomorphin-2 (Antanal-2).

Journal: Journal of medicinal chemistry 20070208

Title: Replacement of the N-terminal tyrosine residue in opioid peptides with 3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid (Dcp) results in novel opioid antagonists.

Journal: Journal of medicinal chemistry 20060824

Title: New 2',6'-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold. Development of unique mu-opioid receptor ligands.

Journal: Journal of medicinal chemistry 20060629

Title: Novel 99mTc-labeled neurotensin analogues with optimized biodistribution properties.

Journal: Journal of medicinal chemistry 20060309

Title: Mitochondria-targeted peptide prevents mitochondrial depolarization and apoptosis induced by tert-butyl hydroperoxide in neuronal cell lines.

Journal: Biochemical pharmacology 20051205

Title: Opioid peptide-derived analgesics.

Journal: The AAPS journal 20050901

Title: Type and location of fluorescent probes incorporated into the potent mu-opioid peptide [Dmt]DALDA affect potency, receptor selectivity and intrinsic efficacy.

Journal: The journal of peptide research : official journal of the American Peptide Society 20050601

Title: A new structural motif for mu-opioid antagonists.

Journal: Journal of medicinal chemistry 20050519

Title: Studies on the structure-activity relationship of 2',6'-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H-Dmt-NH-CH(3).

Journal: Bioorganic & medicinal chemistry letters 20050201

Title: Fluorescent dyes alter intracellular targeting and function of cell-penetrating tetrapeptides.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050101

Title: Opioid receptor binding characteristics and structure-activity studies of novel tetrapeptides in the TIPP (Tyr-Tic-Phe-Phe) series.

Journal: Neuro-Signals 20050101

Title: Tolerance develops in spinal cord, but not in brain with chronic [Dmt1]DALDA treatment.

Journal: British journal of pharmacology 20041201

Title: Cell-permeable peptide antioxidants targeted to inner mitochondrial membrane inhibit mitochondrial swelling, oxidative cell death, and reperfusion injury.

Journal: The Journal of biological chemistry 20040813

Title: Quantitative analysis of [Dmt(1)]DALDA in ovine plasma by capillary liquid chromatography-nanospray ion-trap mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040415

Title: Novel 2',6'-dimethyl-L-tyrosine-containing pyrazinone opioid mimetic mu-agonists with potent antinociceptive activity in mice.

Journal: The Journal of pharmacology and experimental therapeutics 20040401

Title: 2',6'-dimethylphenylalanine (Dmp) can mimic the N-terminal Tyr in opioid peptides.

Journal: Biological & pharmaceutical bulletin 20040201

Title: Dansylated analogues of the opioid peptide [Dmt1]DALDA: in vitro activity profiles and fluorescence parameters.

Journal: Acta biochimica Polonica 20040101

Title: Comparison of [Dmt1]DALDA and DAMGO in binding and G protein activation at mu, delta, and kappa opioid receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20031201

Title: Characterization of the binding of [3H][Dmt1]H-Dmt-D-Arg-Phe-Lys-NH2, a highly potent opioid peptide.

Journal: The Journal of pharmacology and experimental therapeutics 20030801

Title: Highly potent fluorescent analogues of the opioid peptide [Dmt1] DALDA.

Journal: Peptides 20030801

Title: Endogenous opioid peptides contribute to antinociceptive potency of intrathecal [Dmt1]DALDA.

Journal: The Journal of pharmacology and experimental therapeutics 20030501

Title: Structural studies of [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond.

Journal: Bioorganic & medicinal chemistry 20030501

Title: 2,6-Dimethyltyrosine analogues of a stereodiversified ligand library: highly potent, selective, non-peptidic mu opioid receptor agonists.

Journal: Journal of medicinal chemistry 20030227

Title: Transcellular transport of a highly polar 3+ net charge opioid tetrapeptide.

Journal: The Journal of pharmacology and experimental therapeutics 20030101

Title: Quantification of [Dmt1]DALDA in ovine plasma by on-line liquid chromatography/quadrupole time-of-flight mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20030101

Title: Dmt and opioid peptides: a potent alliance.

Journal: Biopolymers 20030101

Title: [2',6'-Dimethyltyrosine]dynorphin A(1-11)-NH2 analogues lacking an N-terminal amino group: potent and selective kappa opioid antagonists.

Journal: Journal of medicinal chemistry 20010913

Title: Novel C-terminus modifications of the Dmt-Tic motif: a new class of dipeptide analogues showing altered pharmacological profiles toward the opioid receptors.

Journal: Journal of medicinal chemistry 20010719

Title: Probing the shape of a hydrophobic pocket in the active site of delta-opioid antagonists.

Journal: Journal of peptide science : an official publication of the European Peptide Society 20010701

Title: Antinociceptive and respiratory effects of intrathecal H-Tyr-D-Arg-Phe-Lys-NH2 (DALDA) and [Dmt1] DALDA.

Journal: The Journal of pharmacology and experimental therapeutics 20010401

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Tags:123715-02-6 Molecular Formula|123715-02-6 MDL|123715-02-6 SMILES|123715-02-6 2,6-Dimethyl-l-tyrosine