Fmoc-O-Phospho-L-tyrosine

Base Information

• Chemical Name: Fmoc-O-Phospho-L-tyrosine
• CAS No.: 147762-53-6
• Molecular Formula: C24H22NO8P
• Molecular Weight: 483.414
• Hs Code.: 29224999
• European Community (EC) Number: 882-209-4
• DSSTox Substance ID: DTXSID80933206
• Nikkaji Number: J2.117.581A
• Wikidata: Q72478809
• Mol file: 147762-53-6.mol

Synonyms:Fmoc-O-Phospho-L-tyrosine;147762-53-6;Fmoc-Tyr(PO3H2)-OH;Fmoc-Tyr(H2PO3)-OH;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-phosphonooxyphenyl)propanoic Acid;Fmoc-O-Phospho-Tyr-OH;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[4-(phosphonooxy)phenyl]propanoic acid;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(phosphonooxy)phenyl)propanoic acid;Fmoc-Tyr(PO)-OH;Fmoc-O-Phosphono-L-Tyr-OH;SCHEMBL1738801;DTXSID80933206;AMXUJIHSMANWDW-QFIPXVFZSA-N;L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-phosphono-;MFCD00235902;AKOS015895487;AM84444;CS-W009624;HY-W008908;AS-71286;EN300-7380205;Fmoc-Tyr(PO3H2)-OH, >=95.0% (HPLC);J-008407;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-phosphotyrosine;N-{[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}-O-phosphonotyrosine;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(phosphonooxy)phenyl)propanoic acid

Chemical Property of Fmoc-O-Phospho-L-tyrosine

Chemical Property:

• Refractive Index: 1.65
• PKA: 1.27±0.30(Predicted)
• PSA: 152.20000
• Density: 1.465 g/cm³
• LogP: 4.08340
• Storage Temp.: −20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 483.10830366
• Heavy Atom Count: 34
• Complexity: 742

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-O-phospho-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)OP(=O)(O)O)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)OP(=O)(O)O)C(=O)O
• Uses: Fmoc-O-phospho-L-tyrosine is used in the synthesis of an asparagine mimetic-containing phosphopeptide as an antagonist of the Grb2-SH2 domain.

Technology Process of Fmoc-O-Phospho-L-tyrosine

There total 6 articles about Fmoc-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: 83.0%

O-phosphono-L-tyrosine (21820-51-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(fluorenylmethyloxycarbonyl)tyrosine-O-phosphate (147762-53-6,178432-30-9)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 2h; pH=8 - 9;

DOI:10.1002/anie.201710269

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → N-(fluorenylmethyloxycarbonyl)tyrosine-O-phosphate (147762-53-6,178432-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphoric acid; phosphorus pentoxide / 24 h / 80 °C / Inert atmosphere

2: triethylamine / acetonitrile / 2 h / 20 °C / pH 8 - 9

With phosphorus pentoxide; phosphoric acid; triethylamine; In acetonitrile;

DOI:10.1002/asia.202000575

Reference yield:

Fmoc-L-Tyr(PO(OEt)2)-OH (178432-28-5) → N-(fluorenylmethyloxycarbonyl)tyrosine-O-phosphate (147762-53-6,178432-30-9)

Guidance literature:

With bis(trimethylsilyl)trifluoroacetamide; trimethylsilyl iodide; In dichloromethane; Yield given; 1.) 0 deg C, 1 h; 2.) room temp., 2 h;

DOI:10.1016/0040-4039(96)00666-1

upstream raw materials:

Fmoc-L-Tyr(PO(OEt)2)-OH

N-Fmoc-Tyr-OH

C₃₀H₃₅NO₅Si

O-phosphono-L-tyrosine

Downstream raw materials:

2-(naphthalen-2-yl)acetyl-(L)-Phe-(L)-Phe-(L)-Lys-(L)-Tyr phosphate

C₅₄H₅₈N₆O₈

Fmoc-FpY