53267-93-9

Usage

Uses

Used in Pharmaceutical Industry:
Boc-O-methyl-L-tyrosine is used as an amino acid building block for the synthesis of peptides. Its role in peptide synthesis is crucial due to the growing peptide drug market, where the fast and reliable synthesis of peptides is of great importance for the development of new therapeutic agents.
Used in Research and Development:
In the field of research and development, Boc-O-methyl-L-tyrosine serves as a key component in the creation of novel peptide-based compounds. Its unique structure allows for the exploration of new peptide sequences and the potential discovery of innovative pharmaceuticals with various applications.
Used in Drug Delivery Systems:
Similar to gallotannin, Boc-O-methyl-L-tyrosine can be employed in the development of drug delivery systems. Its incorporation into these systems may enhance the delivery, bioavailability, and therapeutic outcomes of peptide-based drugs, making it a valuable asset in the advancement of pharmaceutical technology.

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)9-10-5-7-11(20-4)8-6-10/h5-8,12H,9H2,1-4H3,(H,16,19)(H,17,18)/t12-/m0/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 67423-44-3 (S)-2-amino-3-(4-methoxyphenyl)propanoic acid hydrochloride 
• 94790-24-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate 
• 3978-80-1 Boc-Tyr-OH 
• 74-88-4 methyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6230-11-1 O-Methyltyrosine 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 17355-19-0 methyl (S)-2-amino-3-(4-methoxyphenyl)propionate 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 77-78-1 dimethyl sulfate 
• 60-18-4 L-tyrosine 

Downstream Products

• 122900-19-0 N^α-tert-butyloxycarbonyl-O-methyl-(S)-tyrosine methylamide 
• 142995-38-8 Boc-Phe(4-OMe)-NMeBzl 
• 167316-06-5 N--O⁴-methyl-L-tyrosyl>-L-alanine methyl ester 
• 171075-69-7 9-<3-(N-tert-butoxycarbonyl-p-methoxyphenyl-L-alanyl)amino-2-fluoro-2,3-dideoxy-5-O-trityl-β-D-ribofuranosyl>-N⁶,N⁶-dimethyladenine 
• 189163-08-4 [(S)-1-[(S)-2-(1-Benzyl-1H-imidazol-4-yl)-1-((S)-1-{(S)-2-[5-(4-fluoro-benzylcarbamoyl)-pentylcarbamoyl]-1-hydroxy-ethyl}-3-methyl-butylcarbamoyl)-ethylcarbamoyl]-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 251308-33-5 [[2-tert-butoxycarbonylamino-3-(4-methoxy-phenyl)-propionyl]-(3-phenyl-propyl)-amino]-acetic acid methyl ester 
• 77446-77-6 Boc-Tyr(Me)-Phe-Val-Asn-Cys(Bzl)-Pro-Arg(Tos)-Gly-NH₂ 
• 77446-73-2 Boc-Tyr(Me)-Phe-Val-Asn-Cys(Bzl)-Pro-D-Arg(Tos)-Gly-NH₂ 
• 92780-94-4 1,Tyr(Me)⁴,Ile⁸>angiotensin II 
• 57183-05-8 tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate 

Relevant academic research and scientific papers

INHIBITOR OF APOPTOSIS (IAP) PROTEIN ANTAGONISTS

Provided herein are compounds that modulate the activity of melanoma inhibitor of apoptosis (ML-IAP) protein, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome

A series of tripeptidic proteasome inhibitors with furylketone as C-terminus were designed and synthesized. Biochemical evaluations against β1, β2 and β5 subunits revealed that they acted selectively on β5 subunit with IC50s against chymotrypsin-like (CT-L) activity in micromolar range. LC-MS/MS analysis of the ligand-20S proteasome mixture showed that the most potent compound 11m (IC50 = 0.18 μM) made no covalent modification on 20S proteasome. However, it was identified acting in a slowly reversible manner in wash-out assay and the reversibility was much lower than that of MG132, suggesting the possibility of these tripeptidic furylketones forming reversible covalent bonds with 20S proteasome. Several compounds were selected for anti-proliferative assay towards multiple cancer cell lines, and compound 11m displayed comparable potency to positive control (MG132) in all cell lines tested. Furthermore, the pharmacokinetic (PK) data in rats indicated 11m behaved similarly (Cmax, 2007 μg/L; AUC0?t, 680 μg/L·h; Vss, 0.66 L/kg) to the clinical used agent carfilzomib. All these data suggest 11m is a good lead compound to be developed to novel anti-tumor agent.

Design, synthesis and preliminary bioactivity studies of indomethacin derivatives as Bcl-2/Mcl-1 dual inhibitors

Bcl-2 family proteins, which divides into pro-apoptosis proteins and anti-apoptosis proteins, are involved in cell apoptosis progression. As numerous studies illustrated, targeting Bcl-2 family proteins is more and more attractive and practicable to cancer treatment. In this work, we designed and synthesized a series of indomethacin derivatives as new inhibitors for Bcl-2 family proteins. Our results of binding assay to Bcl-2 proteins, MTT assay and apoptotic assay indicated that some compounds had potent binding affinity to Bcl-2/Mcl-1 but not Bcl-XL. Furthermore, compound 8j showed improved anti-proliferative activity than known Bcl-2 inhibitor WL-276.

EPHA4 CYCLIC PEPTIDE ANTAGONISTS AND METHODS OF USE THEREOF

Disclosed herein are compounds and methods of use thereof for the modulation of EphA4 receptor activity. In an aspect, is provided a method of treating or preventing a disease or disorder mediated by EphA4, comprising administering to a subject in need thereof a therapeutically effective amount of a compound as described herein, including certain embodiments, or the structural Formula (I), (l-A), (II), (III), (IV), (IV-1), (V), (Vl-A), (Vl-B), (VII-1), (VII-2), (VIII-1), or (VIII-2), or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof.

Preparation method of O-methyl-threonine/tyrosine

The invention relates to a preparation method of O-methyl-threonine/tyrosine. The preparation method mainly overcomes the disadvantages of the existing method that a toxic reagent is volatile, the reagent is dangerous, the steps are long, the yield is low, and the like. The preparation method of the O-methyl-threonine/tyrosine comprises the following steps: N-t-butyloxycarboryl-threonine/tyrosineis catalyzed by sodium hydroxide and reacts with dimethyl sulfate to generate N-t-butyloxycarboryl-O-methyl-threonine/tyrosine, and then t-butyloxycarboryl is removed from the N-t-butyloxycarboryl-O-methyl-threonine/tyrosine through acid substances to obtain the product O-methyl-threonine/tyrosine. The product has important application in the fields of antibiotics and polypeptide drugs.

4-oxo-alkylated tetramic acid compounds and preparation method thereof

The invention relates to novel compounds and a preparation method thereof. The general structural formula is shown as formula I in the description. Animal experiments prove that the compounds have the effect of saving memories of animal models, are high in safety, have no mutagenicity, can remain in blood for hours after oral administration and intravenous injection, can enter brains and can be used for preparing drugs for treating diseases such as Alzihemer's disease, Parkinson's disease, Huntington's disease, vascular dementia, schizophrenia, autism and the like.

4-oxo-alkylated tetramic acid compound as well as preparation method and application thereof

The invention relates to a novel compound as well as preparation method and application thereof. The structural formula of the novel compound is as shown in a formula I. Animal tests show that the compound provided by the invention has a memory effect of rescuing animal models, is high in security and free of mutagenicity induction, can be retained for hours in blood after oral taking and intravenous injection, can be fed into brains and can be used for preparing medicines for treating senile dementia, Parkinsonism, Huntington diseases, vascular dementia, schizophrenia, autism and the like.

Synthesis, bioactivity, docking and molecular dynamics studies of furan-based peptides as 20s proteasome inhibitors

Proteasome inhibitors are promising compounds for a number of therapies, including cardiovascular and eye diseases, diabetes, and cancers. We previously reported a series of furanbased peptidic inhibitors with moderate potencies against the proteasome b5 subunit, hypothesizing that the C-terminal furyl ketone motif could form a covalent bond with the catalytic residue, threonine 1. In this context, we describe further optimizations of the furan-based peptides, and a series of dipeptidic and tripeptidic inhibitors were designed and synthesized, aiming at improved potency and better solubility. Most of the tripeptidic inhibitors demonstrated improved potency and selectivity as b5 subunit inhibitors in both enzymatic and cellular assays, and good antineoplastic activities in various tumor cell lines were also observed. However, no inhibitory effects were observed for the dipeptidic compounds, which led us to presume that a noncovalent binding mode is adopted. Docking studies and molecular dynamics simulations were carried out to verify this presumption, with results showing that the distance between the furyl ketone motif and Thr1 is slightly too long to form covalent bond.

Synthesis and conformation studies of rubiyunnanin B analogs

Five new analogs 4-8 of rubiyunnanin B (1), mainly modified on the tetrapeptide subunit, were synthesized. These agents 4-8 were substituted d-Ala-l-Ala-l-Tyr(OMe)-l-Ala, d-Ala-l-Ala-l-Phe-l-Ala, d-Ala-l-Ala-l-Try-l-Ala, d-Ala-l-Ala-l-Pro-l-Ala, and d-Ala-l-Ala-l-Ala for the d-Ala-l-Ala-l-N-Me-Tyr(OMe)-l-Ala tetrapeptide subunit. Unlike the natural product, the synthetic agents 4-8 adopt only a single solution conformation, and the central peptide bond in the cyclodityrosine subunit of compounds 4-8 adopt trans stereochemistry. Cytotoxic activities of analogs 4-8 against three human cancer cell lines including A549, BGC-823, and HeLa were evaluated and all the five synthesized peptides exhibited no effects against the test cell lines. These compounds were also evaluated for their antiinsulin resistance and insulin sensitizing activities and none of them showed activity in these assays.

Total synthesis of proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide

Total synthesis of the originally proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide, has been accomplished by using a [(4+1)+3+3]-peptide fragment-coupling strategy and careful examination and optimization