O-Phospho-L-tyrosine

Base Information

• Chemical Name: O-Phospho-L-tyrosine
• CAS No.: 21820-51-9
• Molecular Formula: C9H12 N O6 P
• Molecular Weight: 261.171
• Hs Code.: 29225090
• UNII: 2R86C98KDX
• DSSTox Substance ID: DTXSID00176234
• Nikkaji Number: J208.898C
• Wikidata: Q19805940
• Metabolomics Workbench ID: 38812
• ChEMBL ID: CHEMBL286939
• Mol file: 21820-51-9.mol

Synonyms:Phosphotyrosine;Tyrosine O phosphate;Tyrosine-O-phosphate

Chemical Property of O-Phospho-L-tyrosine

Chemical Property:

• Vapor Pressure: 9.05E-15mmHg at 25°C
• Melting Point: 226-227°C
• Boiling Point: 590.1oC at 760 mmHg
• PKA: 1.24±0.30(Predicted)
• Flash Point: 310.7oC
• PSA: 139.89000
• Density: 1.63g/cm3
• LogP: 0.81280
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly), Water (Slightly, Sonicated)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 261.04022410
• Heavy Atom Count: 17
• Complexity: 309

Purity/Quality:

97% ^*data from raw suppliers

Phosphotyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)OP(=O)(O)O
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)OP(=O)(O)O
• General Description: O-PHOSPHO-L-TYROSINE, also known as phosphotyrosine, is a phosphorylated derivative of tyrosine that plays a critical role in cellular signaling by serving as a key substrate for protein tyrosine phosphatases (PTPases). Its structural and functional mimicry is explored in the development of PTPase inhibitors, which have therapeutic potential for diseases like diabetes, cancer, and osteoporosis. Phosphotyrosine mimetics, such as those derived from phenylalanine, aim to replicate its binding properties or irreversibly inhibit PTPases, though further enzymatic studies were hindered by operational constraints.

Technology Process of O-Phospho-L-tyrosine

There total 6 articles about O-Phospho-L-tyrosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → O-phosphono-L-tyrosine (21820-51-9)

Guidance literature:

With phosphorus pentoxide; phosphoric acid; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201710269

Reference yield: 77.0%

O,O-diethyl 4-(bromomethyl)phenyl phosphate (916661-26-2) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → O-phosphono-L-tyrosine (21820-51-9)

Guidance literature:

O,O-diethyl 4-(bromomethyl)phenyl phosphate; N-(diphenylmethylene)glycine tert-butyl ester; With (11bR)-(-)-4,4-dibutyl-4,5-dihydro-2,6 bis(3,4,5-trifluorophenyl)-3H-dinaphth[2,1-c:1’,2’-e]azepinium bromide; potassium hydroxide; In water; toluene; at 0 ℃; Inert atmosphere;

With trimethylsilyl bromide; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In water; for 0.5h; Reflux;

Reference yield:

phospho-Tyr-Gly-Gly-Phe-Leu-OH (129785-81-5) → Leu-enkephalin (58822-25-6) + O-phosphono-L-tyrosine (21820-51-9) + [des-tyr1]-leucine enkephalin (60254-83-3)

Guidance literature:

With aminopeptidase M (EC_3.4.11.2); 2-amino-2-hydroxymethyl-1,3-propanediol; at 37 ℃; for 1h; pH=7.02; Kinetics;

DOI:10.1016/0024-3205(96)00057-4

upstream raw materials:

N-formyl-L-tyrosine

L-tyrosine

L-tyrosine ethyl ester monohydrochloride

phospho-Tyr-Gly-Gly-Phe-Leu-OH

Downstream raw materials:

tert-butyloxycarbonyl-O-phosphotyrosine

L-tyrosine

2-(naphthalen-2-yl)acetyl-D-Phe-D-PheTyr(phosphate)

Refernces

Design and synthesis of phosphotyrosine mimetics

10.1016/S0960-894X(03)00253-1

The research focuses on the design and synthesis of phosphotyrosine mimetics, which are of significant interest as potential therapeutic agents and research tools for selectively inhibiting protein tyrosine phosphatases (PTPases). These enzymes play a crucial role in regulating tyrosine phosphorylation and cellular function, and their inhibition could have therapeutic potential for diseases such as diabetes, cancer, and osteoporosis. The study involved the synthesis of phenylalanine derivatives, designed to mimic phosphorylated tyrosine or to act as irreversible active site inhibitors of PTPases. Key chemicals used in the synthesis process included Fmoc-l-Tyr-(3-NO2)-OH, CDI, MeOH, SnCl2, phosgene, TsCl, pyridine, SO2Cl2, and various other reagents and solvents. The synthesized compounds were then incorporated into a combinatorial library and screened for their ability to inhibit four phosphatases, showing moderate potency and selectivity, with the type 2d phosphotyrosine mimetic exhibiting the best activity. However, further analysis of enzymatic inhibition was not possible due to the termination of operations at Molecumetics.

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